The Five Monuments of Cycling: Every Race Explained
A race-by-race guide to the five Monuments of cycling, the three riders who won them all, and the British winners from Tom Simpson to Lizzie Deignan.
By CricketTaken EditorialPublished Road Racing Explained22 min read
- Monuments
- 5
- Oldest
- Liège-Bastogne-Liège, 1892
- Riders to win all five
- 3
- Record total
- 19, Eddy Merckx
San Remo, 21 March 2009. After nearly 300 kilometres and close to seven hours of racing, Mark Cavendish ran down Heinrich Haussler in the last metres on the seafront and beat him by the width of a tyre. It was the Manxman's first ride in the race. It made him the second British man, after Tom Simpson, to win one of cycling's Monuments.
The five Monuments are Milan-San Remo, the Tour of Flanders, Paris-Roubaix, Liège-Bastogne-Liège and Il Lombardia. They are the oldest, longest and most prestigious one-day races in professional road cycling, and they are run in that order: the first four between mid-March and late April, the last in October. Two are Italian, two Belgian and one French. No British race is among them and none will join, because the list is closed by age.
The cycling Monuments in order through the season
A rider chasing all five does not get them as a set. He gets four in six weeks, each on different terrain and demanding a different body, and then waits half a year for the fifth.
| Monument | Country | First run | Usual slot | Known as |
|---|---|---|---|---|
| Milan-San Remo | Italy | 1907 | Mid to late March | La Primavera, La Classicissima |
| Tour of Flanders | Belgium | 1913 | Early April | De Ronde |
| Paris-Roubaix | France | 1896 | A week after Flanders | The Hell of the North |
| Liège-Bastogne-Liège | Belgium | 1892 | Late April | La Doyenne |
| Il Lombardia | Italy | 1905 | October | The race of the falling leaves |
The spring sequence is not arbitrary. San Remo opens it because the Riviera is warm in March when Flanders is not. The two cobbled races sit on consecutive Sundays, so the same riders in the same form can contest both, and Liège comes last because by late April the specialists have swapped: the heavy men who rode the stones have gone home and the climbers have arrived from their altitude camps. Easter can nudge a date by a week. The order holds.
- Milan-San RemoMid to late March. The longest of the five, flat for most of its length and decided on two short climbs above the Ligurian coast.
- Tour of FlandersEarly April. Short, steep cobbled climbs in the Flemish Ardennes, taken many times over.
- Paris-RoubaixA week later. Almost flat, with around thirty sectors of cobbled farm track and a finish on an outdoor velodrome.
- Liège-Bastogne-LiègeLate April. Out and back through the Belgian Ardennes over a long succession of climbs.
- Il LombardiaOctober. A climbers' race around Lake Como and the last major event of the year.
The customary order. Exact dates move each year with the UCI calendar and are not given here.
What makes a race a Monument when nobody ever voted on it
There is no definition. The UCI's road regulations do not contain the word as a category, no committee admits or relegates races, and nobody can say with confidence who first used the term or when. It came into general use late, well after the races themselves were a century old, as a way of separating five events from the dozens of others that also call themselves classics.
What the five share can be listed, though, and it comes to four things.
Age is the first. Every one of them was first run between 1892 and 1913. Four of them are older than the Giro d'Italia and two are older than the Tour de France, and all of them came through both world wars. Distance is the second: each is longer than almost anything else in one-day racing, around 240 kilometres at the least and close to 300 at San Remo, which pushes the finale towards the six-hour mark, and well past it at San Remo, into a kind of fatigue that shorter races do not reach. Third, each has kept its ground. The routes are redrawn every year, but Roubaix is still cobbles, Liège is still the Ardennes, Lombardy is still the lakes. The fourth is the hardest to pin down and matters most, the weight a win carries. A rider who wins one Monument and nothing else is remembered for it.
The nearest thing to official recognition sits in the UCI's ranking tables, which in recent seasons have put these five in a one-day tier of their own above the other WorldTour classics. Our guide to how UCI points and rankings work covers that scale.
Why the list stays at five
Plenty of good races are not Monuments. The Amstel Gold Race dates only from 1966. La Flèche Wallonne is old enough to be respectable but much shorter. Paris-Tours is as old as Roubaix and has lost its standing. Strade Bianche, run over the white gravel roads of Tuscany since 2007, is regularly called the sixth Monument by people who love it, and the compliment gives the game away: a race can acquire prestige in twenty years but it cannot acquire a nineteenth century. The World Championships and the Olympic road race are bigger prizes in some respects and are excluded for a different reason. They move every year, and a Monument is a place as much as a race.
Milan-San Remo: the easiest Monument to finish and the hardest to win
First run in 1907 and won that year by the Frenchman Lucien Petit-Breton, Milan-San Remo is close to 300 kilometres long, which makes it the longest one-day race in the professional calendar. In recent years the start has moved out of Milan itself to towns such as Abbiategrasso and Pavia. The name has not changed and neither has the shape.
The shape is the peculiar thing. For about 140 kilometres the race crosses the flat Lombardy plain. It climbs the Passo del Turchino, a long drag that no longer decides anything, drops to the Mediterranean, and turns west along the Ligurian coast for another two hours. There are three small headlands, the Capi, and then, inside the final 30 kilometres, two climbs: the Cipressa and the Poggio di San Remo.
Neither would be categorised in a Grand Tour. The Poggio is under four kilometres long at a gradient most club riders in the Peak District would call a drag. Its summit is about five and a half kilometres from the line, and those kilometres are a fast, twisting descent through glasshouses followed by a short run into town.
That is why the race is so easy to finish and so hard to win. Nothing in the first 270 kilometres is selective, so a hundred riders arrive at the foot of the Cipressa together, tired in the legs and fresh in the head, and thirty of them have a real chance. Six and a half hours of racing is settled in about ten minutes. A pure sprinter can win if his team holds the race together, as Cavendish's did. So can an attacker who gets five seconds over the top of the Poggio, a descender who takes risks nobody will follow, or a rider strong enough to go on the Cipressa and hold off the lot.
The Poggio was added to spoil the sprinters
The organisers have spent decades trying to make the race harder without changing what it is. The Poggio was inserted in 1960 and the Cipressa in 1982, both to break up bunch finishes. Neither has done so reliably. The record of seven wins belongs to Eddy Merckx. Italians call the race La Primavera, spring, and the 1910 edition was run through a snowstorm that only a handful of riders survived to the finish.
The Tour of Flanders and its hellingen
The youngest of the five was first held in 1913, founded by the journalist Karel Van Wijnendaele for the newspaper Sportwereld and won by Paul Deman. It was a Flemish race for Flemish readers from the start, and it is the one Monument that ran through the Second World War without a break.
De Ronde covers roughly 270 kilometres, and for the first two-thirds it wanders across flat farmland. The race is the last 100, in the low range of hills south of Oudenaarde that Belgians call the Flemish Ardennes. Here the roads go over the hills by the shortest line, which means straight up. The climbs are called hellingen. Most are a few hundred metres long, many are cobbled, and the organisers string fifteen or more of them together in loops, so that the same hill may be climbed two or three times.
Three matter more than the rest. The Oude Kwaremont is the long one, more than two kilometres with around a kilometre and a half of cobbles, not savage but relentless, and climbed three times in the modern route. The Paterberg, which follows it, is about 360 metres long with a maximum gradient around 20 per cent. The Koppenberg is steeper again, a sunken lane with a pitch above 20 per cent, so narrow and rough that when one rider puts a foot down everybody behind him walks. It was dropped from the route for years after the Danish rider Jesper Skibby fell there in 1987 and an official's car ran over his bike.
Since 2012 the race has finished in Oudenaarde after a final Kwaremont and Paterberg. Before that the finale ran over the Muur van Geraardsbergen and the Bosberg to Meerbeke, and many Belgians have still not forgiven the change.
What the race means in Flanders is hard to convey to anyone who has watched cycling only from Britain. It is closer to a national day than a sporting fixture. The surface, the tactics and the record-holders are covered in detail in our guide to the cobbled Classics, of which Flanders is the centrepiece.
Paris-Roubaix, the Hell of the North
Two textile manufacturers from Roubaix, Théodore Vienne and Maurice Perez, had built a velodrome and wanted a race to finish on it. The first Paris-Roubaix was held in 1896 and won by the German Josef Fischer. It no longer starts in Paris and has not done since the 1960s; since 1977 the start has been in Compiègne, about 80 kilometres north-east of the capital.
The course is roughly 260 kilometres long and almost flat. What makes it a Monument is underneath the riders. After a first 90-odd kilometres on ordinary roads the route turns on to the first of around thirty sectors of pavé, farm tracks laid with rough granite setts, which together add up to something like 55 kilometres. The best known is the Trouée d'Arenberg, a dead-straight 2.3 kilometres through a forest with roughly 95 kilometres still to race. For decades the bunch hit it at full sprint speed, and from 2024 the organisers altered the approach to slow the entry.
The nickname is widely misunderstood. "The Hell of the North" was coined in 1919, when organisers and journalists drove the route to see whether a race could be held at all and found the countryside of the Western Front: shattered villages, mud, tree stumps, shell holes. It described the war, not the cobbles. It has stuck because the cobbles deserve it.
The finish is unlike any other. Riders come off the last sector, enter the old outdoor velodrome in Roubaix and complete a lap and a half of its concrete track, so a race of five and a half hours or more over broken stone can end in a track sprint between two exhausted men. The winner is given a mounted cobblestone, a tradition dating from 1977. Beside the track stands the communal concrete shower block, each cubicle carrying a brass plate with a past winner's name, though most of the modern peloton now washes on the team bus.
A race where luck has a vote
Roubaix is the Monument in which the strongest rider most often loses. A puncture at the wrong moment, a crash two wheels ahead at the mouth of a sector, a team car stuck behind a split: each has cost somebody the race. The record is four wins, shared by Roger De Vlaeminck and Tom Boonen and still standing after the 2026 edition. Sean Kelly, John Degenkolb and Mathieu van der Poel are among the few to have won it and San Remo, a pairing that says something about how different the two tests are.
Liège-Bastogne-Liège, La Doyenne
La Doyenne, the old lady. Liège-Bastogne-Liège was first run in 1892 as an amateur event and turned professional two years later; the Belgian Léon Houa won the first three editions. It is older than the modern Olympic Games.
The route explains itself in the name. From Liège the race heads south through the Ardennes to Bastogne, near the Luxembourg border, and comes back by a harder road, about 255 kilometres in all. The outward leg is steady. The return holds almost all of the climbs, ten or so of them in the last 100 kilometres: the Côte de Wanne, the Stockeu, the Haute-Levée, the Col du Rosier, and then the one everybody waits for, the Côte de La Redoute, around 35 kilometres from the finish and steep enough over its two kilometres to split the race for good. The Côte de la Roche-aux-Faucons, added in 2008, is now usually the last real climb. For most of three decades the race finished on a drag in the suburb of Ans; since 2019 it has ended back in Liège.
These are not Flemish hills. An Ardennes climb is two to five kilometres long on a wide tarmac road, and the total ascent across the day runs past 4,000 metres, the equivalent of a medium mountain stage in a Grand Tour. That is the reason Liège is the Monument stage racers win. Its roll of honour reads like a list of Tour de France contenders: Merckx, who holds the record with five wins, Bernard Hinault, Alejandro Valverde, Andy Schleck, Primož Roglič, Remco Evenepoel, Tadej Pogačar. Dan Martin, born in Birmingham and racing for Ireland, won it in 2013.
It is also the race with the worst weather stories. In 1980 Hinault rode through a snowstorm that sent most of the field to the team cars, finished more than nine minutes clear, and barely twenty riders reached the line behind him. The cold did lasting damage to the feeling in two of his fingers.
Liège has less glamour than Roubaix and a smaller crowd than Flanders. Riders tend to rate it as the hardest of the five to win on pure strength, because there is nowhere on the way back from Bastogne to hide a weakness.
Il Lombardia, the race of the falling leaves
Autumn sets this one apart. The other four are run when the season is young and everybody is fresh; the Tour of Lombardy, first held in 1905 and won by Giovanni Gerbi, comes in October when the leaves are down, the light goes early and half the peloton is thinking about its holiday. The Italian nickname, la classica delle foglie morte, is literal. Since 2012 the race has been marketed simply as Il Lombardia.
It is the climbers' Monument, more so even than Liège. The route circles Lake Como and the hills between Como and Bergamo, and it changes more from year to year than any of the others: the start and finish have swapped between the two cities, Lecco and Milan have hosted finishes in the past, and the climbs are reshuffled each time. Around 240 to 255 kilometres is typical.
One climb is nearly always there. The road from Bellagio up to the Madonna del Ghisallo rises from the lakeshore to a small chapel at the top, and in 1949 Pope Pius XII declared the Madonna of that chapel the patroness of cyclists. Its walls are hung with bikes and jerseys left by champions, and its bells are rung as the race goes by. Other regular features are less devotional. The Muro di Sormano is a goat track with ramps steeper than 25 per cent, used briefly in the early 1960s, abandoned as absurd and restored in 2012. Finishes in Como usually come after the Civiglio and the short climb of San Fermo della Battaglia.
The record of five wins was set by Fausto Coppi between 1946 and 1954. Pogačar matched it in 2025 by winning the race for the fifth year in a row, a run without precedent in any Monument.
Lombardy has a mood the others lack. Riders announce retirements there. A world champion crowned a fortnight earlier wears the rainbow jersey in it for almost the first time, which is how Simpson won it in 1965. And because it comes after the Grand Tours rather than before them, it is the one Monument in which the form book of the whole season is available to everybody, and still gets overturned.
Which kind of rider wins which Monument
The five races ask for bodies that barely belong to the same sport. Fifteen kilograms can separate a typical Roubaix winner from a typical winner in Lombardy.
| Monument | What decides it | Who tends to win |
|---|---|---|
| Milan-San Remo | Two short climbs and a descent after 270 km | Sprinters who can survive, attackers, descenders |
| Tour of Flanders | Repeated steep cobbled climbs | Powerful classics specialists with a hard acceleration |
| Paris-Roubaix | Long flat cobbled sectors, positioning, luck | Big, heavy riders with high sustained power |
| Liège-Bastogne-Liège | A long series of tarmac climbs | Puncheurs and Grand Tour climbers |
| Il Lombardia | Longer, steeper climbs and technical descents | Pure climbers |
On the cobbles, mass is an asset. A heavier rider with more absolute power holds his speed over rough stone and is deflected less by each impact, and on a flat road his weight costs him nothing. In the Ardennes and above Lake Como every kilogram has to be lifted, repeatedly, so the advantage passes to light riders with a high ratio of power to weight. Milan-San Remo sits oddly between the two: the climbs are gentle enough for a heavy sprinter to survive and short enough for a puncheur to attack on.
That is why so few riders contend at all five. Until the 1980s it was normal for the best to ride everything, and the three men who completed the set all raced in that period. Then came specialisation. Cobbled riders skipped the Ardennes, climbers stayed away from Roubaix for fear of injury before the Grand Tours, and for thirty years a rider who won both Flanders and Lombardy would have been a curiosity.
Two riders have partly reversed that. Pogačar, a Tour de France winner who weighs what a climber weighs, has won the Tour of Flanders three times, added Milan-San Remo in 2026 and finished second at Roubaix in 2025 and 2026. Van der Poel has won the three Monuments that suit a powerful rider and been competitive at Liège. Neither had all five when the 2026 spring Classics ended.
The three riders who won all five Monuments of cycling
Three men, all Belgian. Nobody else.
Rik Van Looy was first. He won Milan-San Remo in 1958, Flanders and Lombardy in 1959, and completed the set with Paris-Roubaix and Liège-Bastogne-Liège in 1961, finishing his career with eight Monument wins. Eddy Merckx collected his five between 1966 and 1971 and did not stop: by the end he had won every one of them at least twice, something no other rider has done, for a record total of 19. Roger De Vlaeminck finished his set at the 1977 Tour of Flanders and ended on 11.
- Milan-San Remo36.8%
- Liège-Bastogne-Liège26.3%
- Paris-Roubaix15.8%
- Tour of Flanders10.5%
- Il Lombardia10.5%
Career totals, 1966 to 1976. Merckx is the only rider to have won each of the five more than once.
Show the numbers
| Item | Value |
|---|---|
| Milan-San Remo | 7 |
| Liège-Bastogne-Liège | 5 |
| Paris-Roubaix | 3 |
| Tour of Flanders | 2 |
| Il Lombardia | 2 |
Merckx's distribution is worth a second look. Seven of the 19 came at San Remo, the race modern riders find hardest to control, and five at Liège. His weakest returns, if two wins can be called weak, were at Flanders and in Lombardy.
Several riders have finished one short, and the missing race is usually the one their build should have predicted.
| Rider | Monuments won | The one missing |
|---|---|---|
| Sean Kelly | San Remo, Roubaix, Liège, Lombardy | Tour of Flanders |
| Philippe Gilbert | Flanders, Roubaix, Liège, Lombardy | Milan-San Remo |
| Hennie Kuiper | San Remo, Flanders, Roubaix, Lombardy | Liège-Bastogne-Liège |
| Louison Bobet | San Remo, Flanders, Roubaix, Lombardy | Liège-Bastogne-Liège |
| Fred De Bruyne | San Remo, Flanders, Roubaix, Liège | Il Lombardia |
| Germain Derycke | San Remo, Flanders, Roubaix, Liège | Il Lombardia |
Pogačar became the seventh rider to hold four of the five when he won at San Remo in 2026; unlike the six in the table, he was still racing, with Paris-Roubaix the one missing.
Kelly's case is the cruellest: the Irishman won nine Monuments and finished second in the Tour of Flanders three times. Gilbert's is the most recent, and the most deliberate. Having won Lombardy and Liège as a puncheur, he remade himself as a cobbled rider in his mid-thirties, won Flanders in 2017 and Roubaix in 2019, and spent his last seasons trying and failing to win the supposedly easiest of the five.
At that point Pogačar had five Lombardias, four Lièges, three Tours of Flanders and one Milan-San Remo, and still needed Roubaix. Van der Poel had three wins at Flanders, three at Roubaix and two at San Remo, and needed the two hilliest. These are snapshots. Check a current results source before quoting either figure.
British results in the Monuments
Britain's record is thin and oddly distinguished. It consists, on the men's side, of two riders.
Tom Simpson, born in County Durham and raised in Harworth in Nottinghamshire, won three different Monuments in five seasons. In the 1961 Tour of Flanders he beat the Italian Nino Defilippis in a two-man sprint on a day when the wind had brought down the finish banner; Defilippis protested that he had not known where the line was, and got nowhere. Simpson won Milan-San Remo in 1964, beating Raymond Poulidor. In 1965, weeks after becoming world champion, he won the Tour of Lombardy alone in the rainbow jersey. No British man has won three Monuments since, or two.
Cavendish's San Remo in 2009 is the other. He was 23, a sprinter widely expected to be dropped on the Cipressa or the Poggio, and he was still in the front group over the top of both.
The women's record is stronger.
| Rider | Monument | Year |
|---|---|---|
| Tom Simpson | Tour of Flanders | 1961 |
| Tom Simpson | Milan-San Remo | 1964 |
| Tom Simpson | Tour of Lombardy | 1965 |
| Nicole Cooke | Tour of Flanders (women) | 2007 |
| Mark Cavendish | Milan-San Remo | 2009 |
| Lizzie Deignan | Tour of Flanders (women) | 2016 |
| Lizzie Deignan | Liège-Bastogne-Liège Femmes | 2020 |
| Lizzie Deignan | Paris-Roubaix Femmes | 2021 |
Lizzie Deignan, from Otley in West Yorkshire, won Flanders in 2016 as world champion, racing then as Lizzie Armitstead, took Liège in 2020 and then won the very first women's Paris-Roubaix in 2021 with a solo attack of more than 80 kilometres in the rain. Like Simpson, she has three different Monuments.
The near misses are a longer list. Barry Hoban was third at Liège in 1969 and at Roubaix in 1972. Roger Hammond finished third at Roubaix in 2004 and Ian Stannard did the same in 2016. Ben Swift was twice on the podium at San Remo, Tom Pidcock was second at Liège in 2023 and second again at San Remo in 2026, and Adam Yates third in Lombardy in 2021. After the 2026 editions no British man had won Paris-Roubaix or Liège-Bastogne-Liège.
One more British footnote. Team Sky won its first Tour de France in 2012 and did not win a Monument until Wout Poels took Liège in 2016. For a squad built on control and calculation, the one-day races proved much harder to buy than July; the Tour side of that story is in our guide to Britain's Tour de France and Grand Tour champions.
The women's Monuments and when each began
Strictly speaking there are none, since the word has no official meaning for either sex. In practice the women's editions of the same races are treated as the equivalent, and they arrived one at a time over two decades.
| Monument | First women's edition | First winner |
|---|---|---|
| Tour of Flanders | 2004 | Zoulfia Zabirova |
| Liège-Bastogne-Liège | 2017 | Anna van der Breggen |
| Paris-Roubaix | 2021 | Lizzie Deignan |
| Milan-San Remo | 2025 | Lorena Wiebes |
| Il Lombardia | None by the end of 2025 | Not applicable |
The Milan-San Remo entry needs a note. A women's race called the Primavera Rosa was run on the Riviera from 1999 to 2005 and then lapsed, so the 2025 event was a return after twenty years rather than a first. Paris-Roubaix Femmes was meant to begin in 2020, was lost to the pandemic and was eventually held in October 2021 on wet cobbles.
The women's races are shorter and that changes them. Paris-Roubaix Femmes has joined the men's route part-way along and in its first six editions, 2021 to 2026, did not include the Arenberg, and the women's San Remo covers roughly half the men's distance, which removes the long attritional approach and makes the Cipressa and Poggio count for more. Flanders and Liège use the same decisive climbs as the men. Most are held on the same day as the men's race or the day before, on the same closed roads and in front of the same crowds, which is the main reason they gained standing so fast.
Where the Monuments sit beside the Grand Tours and the Worlds
Professional road cycling has three kinds of big prize. The Grand Tours last three weeks and reward consistency, recovery and a team that can control a race; our guide to the Tour's distance, stages and days sets out the scale of that. The World Championships are a single race for national teams on a course that changes every year. The Monuments are the third kind: fixed places, one day each, no second chance.
That last point shapes careers. A Tour contender who has a bad day can limit his losses and recover the next afternoon. A classics rider who punctures at the Carrefour de l'Arbre waits twelve months. So riders such as Boonen, Fabian Cancellara and Johan Museeuw built their whole year around six weeks in spring, arrived at the start of March at a peak that could not be held into summer, and never seriously raced for the overall in a Grand Tour. Whole teams are organised the same way, with rosters, budgets and winter training camps aimed at April.
The reverse specialisation is just as real. A Grand Tour leader is paid to be in yellow in July, and his team would generally prefer he did not risk a collarbone on the cobbles in spring. That is what makes it notable when one rides them anyway.
Which matters more is an argument without an answer, but British readers should know that the Tour-first view common here is not shared everywhere. In Flanders a rider who wins De Ronde does not need to win anything else. In Italy the phrase for San Remo is simply la Classicissima. And the men who decide such things by riding, the professionals, have tended to say that a Monument is harder to win than a Grand Tour stage and stays with them longer.
For more on the sport, see our cycling section; the rest of this series is on the England guides hub, and British stage racing is covered in our guide to the Tour of Britain.