ANALYSIS | Three incredible upsets in the 2025 cycling season

The 2025 season will be remembered largely for the commanding wins of Tadej Pogacar and Mathieu van der Poel. But, by no means was this a predictable year, and there were many moments where the script broke down entirely. In races usually shaped by hierarchy, reputation, and team control, three results stood out because they overturned everything the sport had come to expect.

Simon Yates finally won the Giro d’Italia seven years on from a heartbreaking collapse, and he redeemed himself on the very climb that had once crippled him. Mattias Skjelmose defeated Tadej Pogacar and Remco Evenepoel head-to-head at Amstel Gold, on terrain that should have favoured neither hesitation nor surprise. And Neilson Powless dismantled Team Visma | Lease a Bike at Dwars door Vlaanderen, beating Wout van Aert despite being numerically overwhelmed.

None of these outcomes were accidents. Each was the product of specific race dynamics, and each forced a reassessment of assumptions that had guided modern men’s cycling. So, let’s remind ourselves of 3 wonderful surprises in the 2025 cycling calendar.

For Simon Yates, the Giro d’Italia had long been the race that exposed his vulnerabilities. His spectacular collapse in 2018 became part of cycling’s collective memory, and every Giro start since was filtered through that lens. By 2025, Yates was no longer viewed as a natural three-week favourite. He was experienced, dangerous on the right terrain, and a potential podium threat, but widely considered unlikely to win the Maglia rosa.

That perception is what made his overall victory such a shock.

Rather than dominating the race early, Yates rode a controlled and almost understated Giro. He avoided time losses in moments where rivals overreached, stayed clear of chaos on transitional stages, and never appeared tempted to force the issue prematurely. The key difference from previous campaigns was restraint. Where earlier versions of Yates had chased time aggressively, the 2025 version allowed the race to come to him.

Whilst pre-race favourites Primoz Roglic and Juan Ayuso crashed out, and Isaac del Toro and Richard Carapaz focussed on each other, Simon Yates lurked quietly in the shadows. The decisive stages came late, when fatigue rather than ambition shaped outcomes. On the gravel of the Colle delle Finestre, where he had imploded 7 years earlier, Yates came alive and took advantage of Del Toro and Carapaz focussing too much on one another.

With Wout van Aert waiting for him at the top of the climb, Yates rode away to an emotional redemption ride, and the pink jersey that was no nearly his 7 years before. Winning the Giro this way, reframed his career. It was an upset not because Yates lacked talent, but because few believed he could still align his abilities with the Giro’s demands. In 2025, he finally did.

The Amstel Gold Race has increasingly become a playground for the sport’s most explosive superstars. Entering the 2025 edition, the narrative was simple: Tadej Pogacar versus Remco Evenepoel, with the rest of the field expected to respond rather than dictate.

Mattias Skjelmose was not part of that pre-race conversation.

What followed was one of the clearest tactical upsets of the season. Instead of being dropped when the race fractured, Skjelmose remained present at every key moment, and rode with EVenepoel back to Pogacar’s wheel. When Pogacar and Evenepoel attempted to impose their usual rhythm, aggressive accelerations designed to isolate rivals, Skjelmose matched them through positioning rather than raw force.

The crucial moment came down to the sprint. The three riders were locked together, separated by mere centimetres, but to everyone’s surprise it was Skjelmose of Lidl-Trek who outkicked the big boys, by far the biggest win of his young career.

Winning Amstel over those two riders was shocking precisely because it broke a familiar pattern. In recent seasons, races featuring the likes of Pogacar and Evenepoel had been resolved through direct confrontation. Skjelmose turned it into a contest of timing and commitment instead. The result instantly elevated him from respected contender to proven giant-killer, and demonstrated that even the sport’s most dominant figures can be beaten when race dynamics shift against them.

If Amstel Gold was a tactical upset, Dwars door Vlaanderen was a strategic one. Team Visma | Lease a Bike entered the race with numerical superiority and the presence of Wout van Aert, usually a near-guarantee of control.

Instead, Powless read the race perfectly. When Visma attempted to use their numbers to wear down rivals, Powless resisted the temptation to follow every move. He conserved energy, stayed clear of unnecessary efforts, and positioned himself for the decisive phase rather than reacting emotionally to team tactics.

When the race finally split, Powless committed fully, forcing Visma into an uncomfortable position. Their numerical advantage became a liability rather than a strength, as hesitation and internal marking allowed Powless to simply hang on at the back. Soon, it became clear that Van Aert and Visma were going to wait for the sprint, much to Powless delight.

Beating van Aert in this context mattered. Van Aert thrives in attritional races where control and depth decide outcomes. Powless turned Dwars into a test of decisiveness instead, and passed it while Visma hesitated.

For American cycling, it was one of the most significant one-day victories in years. For the season as a whole, it was proof that even the most organised teams can be undone when one rider reads the race better than everyone else.

Taken together, these three moments reshaped the story of 2025. They showed that cycling’s hierarchy is not as fixed as recent seasons suggested, and that timing, patience, and commitment still matter as much as raw dominance. Yates proved experience can still win Grand Tours. Skjelmose showed that even the sport’s biggest stars can be outmanoeuvred. Powless demonstrated that team strength means little if it isn’t converted decisively.

What do you think will be the biggest upset of the upcoming 2026 season?