The Cheltenham Gold Cup isn’t just the most prestigious race in National Hunt racing—it’s also one of the biggest betting spectacles of the year. Every March, millions of pounds are wagered on the Festival’s flagship race, with punters hoping to land a life-changing win or, in some cases, suffering crushing losses.
From stunning 100/1 upsets to heart-stopping near-misses, the Gold Cup has produced some of the most incredible betting stories in racing history. Let’s take a look at the biggest wins, devastating losses, and legendary punts that have shaped Cheltenham Gold Cup betting history.
1. Norton’s Coin (1990) – The Ultimate 100/1 Shock
If there’s one Gold Cup result that sent shockwaves through the betting world, it was Norton’s Coin’s stunning 100/1 victory in 1990.
How It Happened:
- Trained by Sirrell Griffiths, a dairy farmer with just three racehorses, Norton’s Coin was only entered as a late decision.
- He faced Desert Orchid, the reigning Gold Cup champion and heavy favorite at 10/11, expected to dominate the race.
- Against all odds, Norton’s Coin stormed home to win by three-quarters of a length, producing the biggest-priced winner in Gold Cup history.
The Betting Impact:
- A £10 bet on Norton’s Coin at 100/1 returned £1,010, making lucky punters a small fortune.
- Bookmakers cleaned up, as almost all the money had been on Desert Orchid and Toby Tobias, with very few backing the 100/1 outsider.
Norton’s Coin’s victory remains one of the biggest betting upsets in Cheltenham Festival history—a reminder that in racing, anything is possible.
2. Kauto Star & Denman (2008) – The Clash That Cost Millions
The 2008 Gold Cup was one of the most anticipated races in modern history, as stablemates Kauto Star and Denman—two of the best chasers of their generation—went head-to-head.
The Betting Build-Up:
- Kauto Star (10/11 favorite) was the defending champion, known for his blistering speed and tactical versatility.
- Denman (9/4), nicknamed “The Tank,” was an unrelenting galloper, built for pure power and stamina.
How It Played Out:
- Denman ran the race of his life, setting a relentless pace and galloping Kauto Star into submission.
- Kauto Star couldn’t match Denman’s stamina, finishing a distant seven lengths behind his stablemate.
The Betting Fallout:
- Massive losses for punters—so much money had been placed on Kauto Star that bookmakers breathed a sigh of relief when Denman won.
- One punter reportedly lost £200,000 on Kauto Star, convinced he would defend his title.
- On the flip side, one lucky bettor turned £5,000 into £17,500 by backing Denman early at 7/2.
The race cemented one of the greatest rivalries in Gold Cup history, with punters still debating which of the two was the better horse.
3. Lord Windermere (2014) – The 33/1 Gold Cup Stunner
The 2014 Gold Cup delivered one of the most dramatic finishes in Festival history, with Lord Windermere pulling off a stunning last-to-first victory at 33/1.
How It Happened:
- Lord Windermere was completely written off before the race, with form figures that suggested he had no chance.
- For most of the race, he was dead last, showing no signs of getting involved.
- Then, jockey Davy Russell weaved through the field, producing an incredible late charge to snatch victory by just a nose.
The Betting Fallout:
- Lucky punters who had faith in the outsider cashed in massively, with one bettor winning £66,000 from a £2,000 each-way bet.
- Most of the betting money was on Silviniaco Conti (3/1) and Bobs Worth (6/4 favorite), both of whom were beaten.
- Bookmakers celebrated another Gold Cup shock, as Lord Windermere’s win meant huge losses for punters.
His unbelievable last-to-first run remains one of the most dramatic and unlikely Gold Cup victories of all time.
4. Coneygree (2015) – The Novice Who Shocked the Betting Market
When Coneygree lined up for the 2015 Gold Cup, he was a novice chaser with just three previous runs over fences. No novice had won the race since 1974, and most punters expected the more experienced horses to dominate.
How It Happened:
- Instead of waiting behind seasoned rivals, Coneygree set off in front and never looked back.
- His fluent jumping and relentless gallop saw him fend off all challengers, making history as the first novice to win in 41 years.
The Betting Fallout:
- Coneygree won at 7/1, meaning a £10 bet returned £80.
- Many bettors had dismissed him in favor of Djakadam (10/1) and Silviniaco Conti (3/1 favorite).
- One punter reportedly won £50,000 after placing a last-minute bet on Coneygree, recognizing his unbeaten record over fences.
His brave front-running display changed how punters and trainers viewed novice chasers, proving that experience isn’t always essential in the Gold Cup.
5. The £1 Million Near-Miss (2019)
One of the biggest near-misses in Gold Cup betting history came in 2019, when a punter came agonizingly close to landing a £1 million accumulator bet.
The Bet:
- The bettor had placed a £5 accumulator across four Cheltenham races.
- Three of his selections had already won, meaning he only needed Anibale Fly (22/1) to win the Gold Cup to scoop £1 million.
- Anibale Fly ran a fantastic race but could only finish second, losing out to Al Boum Photo.
