Tadej Pogačar has already won the Tour de France three times, the Giro d’Italia, and multiple Spring Classics. But in 2026, the Slovenian superstar has set himself a challenge that no cyclist in the modern era has ever accomplished: winning all five Monuments in a single season.
With Strade Bianche and Milan-San Remo already checked off earlier in the spring, and Tour of Flanders now added to the list, Paris-Roubaix on April 12/13 and Liège-Bastogne-Liège on April 26 are all that stand between Pogačar and the most extraordinary achievement in Monument cycling history. Here’s what you need to know.
What Are the Five Cycling Monuments?
For the uninitiated, the five Monuments are professional cycling’s most prestigious one-day races — events older than most national road cycling federations, with histories dating back to the late 19th and early 20th centuries:
- Milan-San Remo (Italy, March): the longest one-day race on the calendar at ~290km, finishing on the Poggio descent to the Italian Riviera
- Tour of Flanders (Belgium, early April): cobbles and brutal Flemish climbs, finishing on the Oude Kwaremont and Paterberg
- Paris-Roubaix (France, mid-April): “The Hell of the North” — 257km across 29 cobblestone sectors ending in the Roubaix velodrome
- Liège-Bastogne-Liège (Belgium, late April): the oldest Monument, “La Doyenne,” a brutal 258km through the Ardennes hills
- Il Lombardia (Italy, October): the “Race of the Falling Leaves,” through the mountains around Lake Como
No cyclist in the modern era has won all five in the same season. Eddy Merckx came closest, winning four in 1975. Roger De Vlaeminck won all four of the Cobbled Classics multiple times but never completed the set. The feat requires a rider to excel across cobbles, climbs, endurance, and sprint finishes — almost contradictory demands.
Pogačar’s 2026 Spring Campaign So Far
Pogačar has been masterful through the early spring. His Strade Bianche win in March showed his white-road versatility. Milan-San Remo — where he had previously finished on the podium multiple times — finally came his way. And then came Tour of Flanders, where he navigated cobbles and steep Flemish climbs that many pure climbers simply cannot handle.
Three down. Two to go.
Paris-Roubaix: The Biggest Unknown
Paris-Roubaix, scheduled for April 12/13, represents Pogačar’s biggest challenge in the five-Monument quest. “The Hell of the North” isn’t just a punishing race — it’s one that often comes down to mechanical fortune, bike-handling skill on cobblestones at 45kph, and the specific physical capacity to absorb hours of jarring vibration while maintaining sprint power.
Pogačar has shown he can handle cobbles — Tour of Flanders is proof. But Roubaix’s 29 sectors of pavé, covering more than 54km of the race distance, are categorically different from the Flemish bergs. The sector ratings run from one star (rough) to five stars (brutal), with the Arenberg Forest sector — a 2.4km stretch that can destroy a race in seconds — being the most feared.
Teams run 30-32mm tyres at 3.5-4.0 bar for maximum cushioning. Even so, mechanical failures are endemic. Riders carry up to three spare wheels in team cars. The race demands that a sporting genius also be an incredibly lucky one.
Liège-Bastogne-Liège: Where Pogačar Thrives
If Roubaix is the wildcard, Liège (April 26) is where Pogačar should be the overwhelming favourite. “La Doyenne” — the oldest race in professional cycling, first held in 1892 — plays directly to his strengths: sustained climbing, explosive acceleration on steep hills, and the ability to time an attack with devastating precision.
The race covers 258km through the Ardennes hills of Belgium, climbing La Redoute (2km at 8.9% average), Roche aux Faucons, and finishing on the Côte de la Roche-aux-Faucons before returning to Liège. It’s a race that punishes riders who’ve already exhausted themselves on Roubaix the week before — which is why completing the double in a single year is so rare.
Remco Evenepoel (Soudal Quick-Step), fresh from his World Championship performances, will be the primary rival. The Belgium-versus-Slovenia subplot adds edge to what is already one of the best rivalries in the sport.
What This Means for Cycling’s Historical Narrative
Should Pogačar complete the five Monuments in 2026, it would stand as arguably the greatest single-season achievement in the history of road cycling. Even winning four would place him alongside Eddy Merckx — the “Cannibal” who dominated the sport in the 1970s and whose records have stood for half a century.
The fact that it’s happening in an era of increased competition, more sophisticated team tactics, and arguably deeper fields than Merckx faced makes it all the more remarkable. We’re watching something potentially historic unfold in real time.
For those just getting into pro cycling, our race preparation guide offers insight into how professional racing demands translate to amateur training principles. And our overview of the Women’s WorldTour 2026 highlights equally compelling storylines unfolding on the women’s side of the sport.
Key Dates to Watch
- Paris-Roubaix Women’s: Saturday April 12, 2026
- Paris-Roubaix Men’s: Sunday April 13, 2026
- La Flèche Wallonne: Wednesday April 22, 2026
- Liège-Bastogne-Liège: Sunday April 26, 2026
Key Takeaways
- Tadej Pogačar has won Strade Bianche, Milan-San Remo, and Tour of Flanders in 2026 — three of the five Monuments
- Paris-Roubaix (April 13) and Liège-Bastogne-Liège (April 26) remain; winning all five would be unprecedented in the modern era
- Roubaix is the biggest wildcard — cobblestone chaos favours mechanical luck as much as athletic talent
- Liège is Pogačar’s strongest suit; Remco Evenepoel is the main rival
- No modern-era rider has won all five Monuments in a single season; Eddy Merckx came closest with four in 1975
