Pogacar's Grand Slam: Can He Win All Five Monuments in a Single Season?
Two down, three to go. When Tadej Pogacar soloed across the finish line in Oudenaarde on Easter Sunday to claim his record-equalling third Tour of Flanders, he didn't just add another Monument to his palmarès — he lit a fuse under the most extraordinary question professional cycling has ever confronted. Can one rider win all five Monuments in a single calendar year? No one in the sport's 150-year history has ever done it. But after Milan-San Remo in March and Flanders last Sunday, Pogacar is halfway there, and the remaining three — Paris-Roubaix, Liège-Bastogne-Liège and Il Lombardia — are all races he has either won before or targeted with meticulous preparation.
The scale of this ambition needs historical context. Only three riders in the entire history of the sport have won all five Monuments across their careers: Rik Van Looy, Eddy Merckx and Roger De Vlaeminck. Each took years to assemble the full set. Van Looy needed eight seasons. Merckx, the greatest cyclist who ever lived, took six. Pogacar completed the career set with his Milan-San Remo breakthrough last month — and he is now attempting to compress what took legends decades into a single, breathtaking spring and autumn campaign.
The first test of the quest's viability comes this Sunday at Paris-Roubaix, and it is arguably the hardest. The Hell of the North is the most unpredictable of the five Monuments — a 257km war of attrition across 54.5km of cobbled sectors where punctures, crashes and mechanical failures routinely eliminate the strongest rider in the race. Mathieu van der Poel has won the last three editions and possesses an almost supernatural ability to read the cobbles at speed. Pogacar finished second on his debut last year after misjudging a turn with 40km to go — agonisingly close, but a reminder that raw power alone does not guarantee success on the pavé. UAE Team Emirates-XRG have invested heavily in cobblestone specialists like Florian Vermeersch, and Pogacar has completed four reconnaissance trips to northern France this year alone. The intent is unmistakable.
If he survives Roubaix, the Ardennes Classics two weeks later should represent more familiar territory. Pogacar has won Liège-Bastogne-Liège three times and his uphill finishing ability on the Côte de la Roche-Aux-Faucons makes him the overwhelming favourite every time he lines up. Remco Evenepoel and Isaac del Toro will provide stern opposition, but on the hilly Ardennes terrain Pogacar's combination of explosive climbing and tactical intelligence has proven all but unbeatable.
The final piece, Il Lombardia in October, is perhaps the most statistically favourable. Pogacar won three consecutive editions from 2021 to 2023 and his mastery of the race's decisive San Fermo della Battaglia climb is well-documented. The six-month gap between the spring and autumn Monuments introduces a wildcard — form, fatigue and the small matter of the Tour de France all intervene — but if Pogacar arrives at Lombardia healthy and with four Monuments already in the bag, the pressure to complete the set will be enormous for both him and his rivals.
The cycling world is divided on whether it can happen. Cyrille Guimard, the legendary French directeur sportif, told Belgian media this week: "If he wins all five, he should stop right away — there would be nothing left to achieve." The quote captures the unprecedented nature of the challenge. Merckx himself, asked about Pogacar's chances after Milan-San Remo, was characteristically generous: "It is now clear that he has no limits." The Escape Collective's analysis took a more measured tone, arguing that the sheer volume of racing and the chaos inherent in Paris-Roubaix make it statistically improbable — but even their scepticism was tempered by the acknowledgment that Pogacar has spent 2026 systematically dismantling records once thought untouchable.
What makes this quest different from hypothetical discussions of previous eras is the deliberateness of Pogacar's approach. This is not a rider stumbling into history. He chose to skip a fifth Tour de France title bid to focus on Roubaix. He has overhauled his equipment specifically for the cobbles. He has structured his entire 2026 season around maximising his Monument opportunities. The grand slam is not a fantasy he entertains in press conferences; it is the organising principle of his year.
Paris-Roubaix on April 12 will provide the definitive first test. If the Hell of the North delivers him a victory, the conversation will shift from "can he?" to "who can stop him?" And cycling will hold its collective breath from April to October, watching a 27-year-old Slovenian attempt something that the greatest riders in the sport's history never dared to try.