Astonishing Wins at Long Odds

Cheltenham has witnessed some extraordinary victories by horses that were given little chance of success. One of the most memorable upsets occurred in 1990 when Norton’s Coin, a 100/1 outsider, won the Cheltenham Gold Cup.

This victory stunned the racing world and remains one of the biggest surprises in the festival’s history. The horse, trained by the relatively unknown Welsh farmer Sirrell Griffiths, outran the more fancied competitors, leaving festival punters and experts alike in disbelief.

Famous Favorites That Faltered

While long-shot winners capture headlines, the failures of heavily-backed favorites can be equally shocking. One such instance was the fall of Annie Power at the 2015 The 2025 Cheltenham Festival.

The mare was a strong favorite in the Mares’ Hurdle but dramatically fell at the last hurdle when leading the race. This unexpected turn of Grade 1 events not only cost festival punters millions but also altered the course of the festival’s Cheltenham betting landscape.

Weather and Track Surprises

Weather conditions and track changes have played significant roles in some of Cheltenham’s biggest Cheltenham betting upsets. The unpredictable British weather can turn a race on its head, as seen in the 2008 Gold Cup. Heavy rain turned the ground soft, favoring horses that were not initially look out fored contenders. This led to Denman, a horse with a reputation for thriving in such conditions, winning against the race odds.

Impact of Jockey Decisions

Jockeys often make split-second decisions that can change the outcome of a race dramatically. A notable example is the 2014 Champion Hurdle, where jockey Barry Geraghty’s tactical brilliance on Jezki led to a surprise victory over the favorite, Hurricane Fly. Such decisions highlight the importance of Festival experience and staking plan, often leading to unexpected results that defy pre-race Cheltenham betting predictions.

Lessons for Festival Punters

The history of Cheltenham betting upsets offers valuable lessons for festival punters. It underscores the importance of look out foring factors beyond just form and race odds, such as weather conditions, track preferences, and jockey Festival experience. Of course, these upsets remind us that in horse racing, nothing is guaranteed, making it essential for jumps fans to manage their likelihood and approach each race with an open mind.