From 1876 to today: the 10 oldest races in pro cycling

First run in 1907 by the Antwerp branch of the Belgian cycling federation, Scheldeprijs predates the Tour of Flanders and stands as the oldest race in the region. The inaugural edition began and ended in Antwerp, finishing on the boards of the now-demolished Zurenborg velodrome, where Frenchman Maurice Léturgie claimed victory.

For decades, Scheldeprijs remained a largely Belgian affair. It took 46 years before another foreign rider won, when Dutchman Hans Dekkers broke the monopoly in 1953. While the start location shifted over time from central Antwerp to its outskirts and back again in 1996, the race retained its identity as a flat, fast contest on exposed Flemish roads.

Originally a summer event, Scheldeprijs found its modern place on the calendar in the 1980s, moving to spring. Since 2010, under the ownership of Flanders Classics, it has been held midweek between the Tour of Flanders and Paris–Roubaix. Today, it is regarded as the sprinters’ classic and often sees the very best on its startlist every year. It’s a major race for the sprinters to win, and German powerhouse Marcel Kittel holds the record for most wins with five.

Milan-San Remo was first held in 1907 after journalist Tullo Morgagni of La Gazzetta dello Sport proposed a one-day race linking Milan’s cycling heartland with the Riviera resort of Sanremo. The first edition rolled out before dawn on 14 April 1907, with just 33 riders starting a 286km journey in tough conditions. Only 14 made it to the finish, where Frenchman Lucien Petit-Breton claimed victory. 

Commercial success quickly followed, and Milano–Sanremo soon became a fixture of the spring calendar, earning the nickname La Classicissima. Traditionally raced on March 19 and finishing on Sanremo’s Via Roma, Eddy Merckx holds the record for most wins with seven.

Despite some minor changes, Milan-San Remo has remained loyal to its roots. The long, mostly flat route is punctuated by the Cipressa and the Poggio, preserving its identity as a rare sprinters’ Monument, where patience, positioning and timing are all crucial skills required to win. Though recent editions illustrate that it isn’t currently a race for the sprinters, with the likes of Tadej Pogačar and Mathieu van der Poel lighting the race up from far out.

The Giro del Piemonte, known now as Gran Piemonte, was first run in 1906, with Giovanni Gerbi claiming the inaugural victory and helping to establish the race’s early prestige. Traditionally held at the tail end of the season, it has often been scheduled just days before Il Lombardia, making it a natural prologue to the final Monument of the year.

Giovanni Gerbi, Costante Girardengo, Aldo Bini, Gino Bartali and Fiorenzo Magni are currently the race’s most successful riders, each recording three victories. The event also carries a sombre chapter: in 1951, Fausto Coppi’s younger brother Serse died from a brain haemorrhage after crashing during the race, passing away a few hours after the finish. On several occasions, Gran Piemonte has ventured beyond Piemonte itself, crossing into the Aosta Valley and finishing in Saint-Vincent.

The most recent edition, held in October 2025, was won by Isaac del Toro, during a remarkable run in which he claimed seven Italian one-day victories in little more than a month.

The Tour of Lombardy, known as the “Race of the Falling Leaves,” was created in 1905. Journalist Tullo Morgagni persuaded La Gazzetta dello Sport to organise a one-off race around Milan as a rematch for local rider Pierino Albini and Giovanni Cuniolo after the Coppa del Re.  Instead, the inaugural Milano–Milano was won decisively by Giovanni Gerbi, who finished nearly 40 minutes clear and immediately gave the event credibility.

The race quickly became the traditional curtain-closer to the European season and was renamed the Giro di Lombardia in 1907. For much of the 20th century, it was known as il Mondiale d’Autunno — the unofficial world championship of autumn. From 1988 to 2004, Lombardia formed the final and often decisive round of the UCI Road World Cup, before emerging as the last remaining Monument of the year. 

Now raced in late September and officially titled Il Lombardia, it's a climbers’ classic defined by climbs like the Muro di Surmano and technical descents where the race can also be won or lost. In 2025, Tadej Pogačar became the first rider to win five consecutive editions of a monument when he soloed emphatically to victory in Bergamo. He holds the record for most wins at the race alongside Fausto Coppi with five.

The greatest cycling event of them all was first held in 1903, and like many races, it was a newspaper that led to its creation. French newspaper L’Auto was formed in 1899 to usurp Le Vélo, the first and biggest daily sports newspaper in France.

Henri Desgrange was appointed as the editor for L’Auto, but a crisis meeting was held in 1902 as the paper wasn’t competing well with its rival in terms of sales. During the meeting, 26-year-old chief cycling journalist Géo Lefèvere came up with a suggestion of forming a six-day race of long-distance stages all around France.

The concept was brought to reality in 1903 with a six-stage event that began in Paris on 31 May, and visited cities including Lyon, Marseille, Bordeaux and Nantes, before returning and before returning to finish in the French capital on 5 July. Such were the distances, stages would go into the night and finish the following afternoon, and ultimately Maurice Garin would go on to win the inaugural edition.

Four riders hold the record for most wins at the Tour de France with five editions each. The first to achieve this milestone was Jacques Anquetil from 1957-1964. He would be joined by Eddy Merckx, Bernard Hinault and Miguel Indurain. Tadej Pogačar could join this exclusive club if he wins in 2026, as the Slovenian currently has four editions to his name.

Another race organised by the French newspaper Paris-Vélo, Paris-Tours, was first run as an amateur event in 1896. One of the purposes of the race was to inaugurate the velodrome in Tours, with the inaugural edition won by Eugène Prévost.

Following the inaugural edition, there was a five-year hiatus before the race returned, with another five years before it became an annual fixture for professionals with L’Auto as the organisers.

The race is historically known as the sprinters' classic, predominantly finishing along the 2.7km long Avenue de Grammont. 

Things have changed in recent years with the finish moving in 2011, and the introduction of gravel sectors in 2018, becoming one of the most entertaining races at the end of each season in mid-October.

The race was a concept created by Roubaix textile manufacturers Théodore Vienne and Maurice Perez, who had just opened a new velodrome in 1895. Looking to put their industrial town on the map, they came up with the idea to host a road race from Paris to their Velodrome. With help from the newspaper Le Vélo, the plan became reality despite doubts over the punishing route and Roubaix’s unfashionable status as a finish.

The first edition covered 280 kilometres and was won by Germany’s Josef Fischer. Riders were forced over rough cobblestones simply because that was the state of the roads, but those stretches of pavé soon defined the race. After World War I, as the route cut through devastated landscapes, Paris–Roubaix earned its lasting nickname: L’Enfer du Nord, the Hell of the North.

Today, the cobbles are still the main attraction. In the 2025 men’s edition, there were 55.3km of cobblestoned sections (pavé) for the riders to contend with. Carefully maintained by volunteers, they continue to define Paris-Roubaix as one of the toughest races on the calendar with more editions being held than any other race on this list with 122.

First held in 1893, Paris-Brussels was some distance away from what the race is like today. Back then, the race was an amateur event, contested over a mammoth 397km and organised French newspaper Le Vélo and the Belgian club Union Vélocipédique Belge. 

The inaugural edition was won by Belgian rider André Henry, before the race took a decade-plus hiatus until 1906, when the format changed into a two-day event. This quickly changed back into the one-day format we know today, and over the coming years, the race would establish itself as a key fixture during the Spring Classics, between Paris-Roubaix and Gent-Wevelgem.

The race struggled for a period during the 1960s due to traffic problems between the two cities of Paris and Brussels, with the Amstel Gold Race taking its place on the calendar. 

However, the race reestablished a strong reputation and is now known as the Brussels Cycling Classic since 2013, with the race taking place entirely in Belgium.

Liège-Bastogne-Liège is the oldest of the five monuments and has the fitting nickname of ‘La Doyenne’ or 'The Old Lady’. This Ardenne classic was first held in 1892 after being created by the French-Belgian newspaper L’Express. The first edition actually began in Spa, the city where the Belgian Grand Prix in Formula 1 is now held, and finished in Bastogne.

The inaugural race reflected cycling's elite status in the late 19th century, described as a "gentlemen's affair" due to the expense of bicycles at the time. Thirty-three riders from local cycling clubs, Liège cycling union, and the Pesant Club Liégois participated, with only 17 completing the 250km route.

Léon Houa, a Liège native, won this first edition after 10 hours and 48 minutes, with the second-place finisher Léon Lhoest arriving 22 minutes later. The race used Bastogne's train station as its turning point, with some exhausted competitors abandoning there and catching the train back to Spa. The 1908 edition marked the first time that Liège hosted both the start and finish of the race and saw the Frenchman André Trousselier win. 1969 saw Eddy Merckx make his mark on the race, winning the first of what would be a record-breaking five editions of La Doyenne, which still remains the most in the race’s history.

The finish location was moved to Ans after the Pesant Club Liégeois partnered with the Société du Tour de France in 1990, overhauling the race. The finish returned to Ans in 2019, where Jakob Fuglsang soloed to victory, though the Dane almost came a cropper on the final descent to the finish.

Since then, Primož Roglič won in 2020 from a small group sprint, after the then World Champion Julian Alaphilippe celebrated too early, whilst the past five editions have seen Remco Evenepoel (2) and Tadej Pogačar (3) share the spoils between themselves.

The world’s oldest bike race, which is still held today, is Milano-Torino. It’s fair to say that the race has changed since the first edition in 1876, when eight riders took to the start, with four finishers. Paolo Magretti, who was a cyclist alongside his primary role as an entomologist, was the winner of the inaugural edition, in a time of 10 hours and nine minutes, over an hour ahead of the second-place rider finishing atop the Superga climb, which has become synonymous with the race.

The next five editions took place sporadically from 1893 until 1911, with Frenchman Henri Pélissier, the 1923 Tour de France champion, becoming the first foreign winner of Milano-Torino. In 1913, Milano-Torino became an annual fixture, with Giuseppe Azzini taking the victory with only brief pauses in the 1920s, 1940s due to World War 2, and from 2008-2011.

In 105 editions of the race, Italian rider Costante Girardengo holds the record for most victories with five. The home nation, Italy, are also convincingly the most successful nation at the race with 76 victories, with Spain and Switzerland tied in second with five.

The position of the race in the calendar has changed multiple times. Up until 1987, the race was held seven days before Milan San Remo, but was moved to October for that year’s edition. Since then, the race has fluctuated between the traditional month of March and the Autumn affair, with the most recent editions taking place in March.

The 2020s have even seen some significant route changes with the removal of the Superga climb, and a flatter route seeing victories for sprinters Arnaud Démare in 2020, Mark Cavendish in 2022 and Arvid De Kleijn in 2023. 

The Superga climb returned for the finale of the 105th edition in 2025, won by Isaac del Toro, who became the first Mexican and fifth non-European to do so, after outsprinting Ben Tulett in the uphill finish in Turin.