Simon Yates: Five moments that defined a brilliant career

From his breakthrough white jersey at the Tour de France to his crowning Giro d'Italia victory in 2025, Yates carved out a legacy built on attacking racing and an unwavering belief in his climbing legs. Now, after announcing his retirement, these are the five moments that defined his career.

Yates saved the best for near last, finally claiming the Maglia Rosa after the nightmare of the Colle de Finestre in 2018, where Yates had looked to go on to win the Giro until the Brit endured one of the biggest collapses for a race leader in cycling history, with Chris Froome taking home the GC after a quite heroic performance on the same stage as Yates' collapse.

After years of near misses, heartbreak and what ifs at the Giro, the British climber delivered a masterclass in three-week racing, staying within the grasp of the contenders, who were Isaac del Toro and Richard Carapaz. Yates seized the moment and took advantage of a squabble between Del Toro and Carapaz on stage 20, on the famed Finestre, with his Visma teammate Wout van Aert ahead, creating a gap of 3:56 over Del Toro in 2nd.

For a rider who had worn pink for 13 days in 2018, only to see it slip away, finally standing atop the podium in Rome closed a chapter and winning on the climb which robbed him of the chance to win his first Grand Tour.

It also cemented his place in British cycling history as one of only a handful of riders to win multiple Grand Tours, and the second Briton to conquer both the Giro and Vuelta. Not bad for a career finale, is it?

Just months after his Giro heartbreak, Yates arrived in Spain with something to prove. What followed was a display of controlled aggression and tactical nous that delivered the red jersey and announced him as a Grand Tour champion. Unlike the fireworks of his Giro campaign, Yates rode with calculated precision, banking time when opportunities arose and defending with intelligence when rivals attacked.

Three-stage victories punctuated his march to Madrid, showcasing the explosive acceleration that made him so dangerous on mountain finishes. The win was particularly sweet given the context: bouncing back from devastation in Italy to claim his first Grand Tour title in Spain demonstrated mental resilience that would define the rest of his career.

At just 26, Yates had achieved what many riders never do, and he did it with a style that thrilled fans. Attacking racing combined with the maturity to know when to hold back. It was the perfect response to those who questioned whether he had the head for Grand Tour racing after the Giro collapse.

Yates never quite cracked the Tour de France GC puzzle, but his 2019 Pyrenean stage double proved he could win on cycling's biggest stage. Both victories came from long-range breakaways, showcasing not just his climbing prowess but his tactical acumen and ability to read a race from distance.

Stage 12 to Bagnères de Bigorre saw Yates attack from the break on the Col du Tourmalet, soloing to victory on Bastille Day. Three days later, he did it again, winning stage 15 to Foix Prat d'Albis with another perfectly timed move. The back-to-back Pyrenean wins announced Yates as a stage hunter of the highest calibre, capable of winning at the Tour even when GC glory eluded him.

What made these wins particularly special was the context. Yates had arrived at the Tour without the pressure of GC expectations, freeing him to race aggressively and hunt stages. It proved a formula that would serve him well throughout his career, and cemented his status as one of the few riders to have won stages at all three Grand Tours.

Before the Grand Tour victories and the stage wins came the breakthrough. Yates's white jersey at the 2017 Tour de France announced his arrival as a Grand Tour contender and set the template for everything that followed. Seventh overall and best young rider at cycling's biggest race was no small achievement for a 24-year-old in just his second Tour appearance.

What impressed most was Yates's consistency across three weeks in the mountains. He didn't have one explosive day; instead, he was there or thereabouts on every major climb, accumulating time through steady, intelligent racing. It was a performance that suggested he had the engine and the head for Grand Tour racing, even if the full package would take a few more years to develop.

The white jersey also marked the beginning of one of cycling's great sibling rivalries, with twin brother Adam finishing in ninth place overall. For British cycling fans, it was a glimpse of a future where the Yates twins would dominate Grand Tour racing for years to come. While Adam would go on to win his own Grand Tours, it was Simon who delivered the more explosive, attacking racing that made him a fan favourite around the world.

Though it ended in heartbreak, Yates's 2018 Giro remains one of the most electrifying Grand Tour performances of the modern era. For 13 glorious days, the British climber wore pink and attacked with a freedom and confidence that lit up the race. His three-stage victories on the volcanic slopes of Etna, the punchy finish at Osimo, and the brutal mountain top at Sappada showcased climbing that few could match.

Yates didn't just defend the jersey; he attacked from it, a rarity in Grand Tour racing, at a time when leaders often rode conservatively. His willingness to take the race to rivals, even from the front, made him a fan favourite and established his reputation as one of cycling's most exciting riders. Watching Yates in pink was appointment viewing; you simply never knew when he'd launch another devastating acceleration.

The final week's collapse, when he cracked spectacularly on the Finestre and tumbled out of contention, was devastating. Yet even in defeat, the 2018 Giro defined Yates as a rider willing to race on the front foot. It also set up one of the great redemption stories when he bounced back to win the Vuelta just months later, and ultimately the Giro itself seven years on.

Also read:
Simon Yates' quiet, surprising farewell was true to his story
Closing the circle - Simon Yates, the Colle delle Finestre and Giro d'Italia redemption