Horse Racing’s Biggest Shocks: When Great Horses Were Beaten

In horse racing, nothing is guaranteed. Not even the greatest champions are immune to defeat. Whether through tactical misjudgments, unsuitable ground, or just being outperformed on the day, some of the sport's biggest names have come unstuck in the most unexpected of ways. Here’s a look at the most famous and shocking defeats in racing history — moments when the unthinkable happened.

Brigadier Gerard – York, 1972 Benson & Hedges Gold Cup
Unbeaten in 15 starts and considered one of the greatest British racehorses of all time, Brigadier Gerard looked unbeatable. But at York, US challenger Roberto, under Braulio Baeza, led from the front and delivered a stunning three-length win, handing Brigadier Gerard the only defeat of his career.

Dancing Brave – 1986 Breeders' Cup Turf (Santa Anita)
After his famous Arc de Triomphe win, Dancing Brave was expected to add the Breeders’ Cup Turf to his glittering CV. But tight turns and firm ground worked against him, and he could only manage fourth behind Manila — a disappointing swansong for a modern great.

Shergar – 1981 St Leger, Doncaster
Following runaway wins in the Epsom Derby, Irish Derby and King George, Shergar was expected to cruise to glory in the final Classic of the season. But the extra distance of the St Leger and softer ground found him out. He weakened in the closing stages and finished a well-held fourth, in what would prove to be his final race.

Annie Power – 2015 Mares' Hurdle, Cheltenham
On the verge of completing a four-timer for Willie Mullins and Ruby Walsh on Cheltenham's opening day, Annie Power led by several lengths into the final hurdle. But in a dramatic twist, she clipped the top and fell — a moment that reportedly saved bookmakers up to £50 million.

Istabraq – 2002 Champion Hurdle, Cheltenham
A three-time Champion Hurdle winner, Istabraq returned to Cheltenham aiming for a historic fourth. But something wasn’t right. After just two hurdles, Charlie Swan pulled him up. He was retired immediately after — a shocking but dignified end to a brilliant career.

Douvan – 2017 Champion Chase, Cheltenham
Arriving unbeaten in 13 races, Douvan was seen as a certainty in the Champion Chase. But after an early mistake, he never travelled and finished seventh. A post-race vet check revealed a stress fracture to his pelvis, but the damage to his aura of invincibility had been done.

Denman – 2005 Royal & SunAlliance Novices’ Hurdle, Cheltenham
Before becoming the “Tank” of staying chasers, Denman was heavily backed to win at the Festival as a novice hurdler. Despite leading at the last, he couldn’t handle the finishing pace of Nicanor, and had to settle for second. He’d have his redemption at the same course over fences in the 2009 Gold Cup — but this was a real shock at the time.

Hurricane Fly – 2014 Champion Hurdle, Cheltenham
Two-time Champion Hurdler Hurricane Fly came into the 2014 edition on a wave of support. But his turn of foot deserted him on the day, and he had to settle for fourth behind fellow Irish-trained Jezki.

These weren’t just unexpected losses — they were big moments in racing history. They remind us that even the most brilliant horses are vulnerable to conditions, competition, and chance. And that’s why we keep coming back — because in horse racing, greatness isn’t guaranteed, and shocks are always waiting just beyond the final furlong.