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Cheltenham Festival: Greatest Gold Cup Winners from Golden Miller to Kauto Star

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Gold Cup greats

The Cheltenham Festival is considered the pinnacle of jumps racing with the best National Hunt horses heading to Prestbury Park each March to contest in 28 races across four days.

There are many top races over the meeting, but it’s the Boodles Cheltenham Gold Cup, which is always run on the final day (Friday) that is the Festival highlight.

Over the years we’ve seen many top staying chasers etch their names in the Cheltenham Gold Cup history books – including five-time winner Golden Miller, plus Mill House, Arkle, Desert Orchid, Best Mate, Kauto Star, Denman and Al Boum Photo.


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Golden Miller1932, 1933, 1934, 1935, 1936

Owned by Dorothy Paget, this Gold Cup legend is the most successful horse in the race’s history with five wins on the bounce between 1932 and 1936.

He also landed the Grand National in 1934 to record a famous Gold Cup/National double.

When he eventually retired in 1939, Golden Miller finished with a race record of 29 wins from 52 races (56% winning strike-rate).

Golden Miller’s owner – Dorothy Paget – went onto win the Cheltenham Gold Cup twice more with Roman Hackle (1940) and Mont Tremblant (1952).


Did you know? Golden Miller was bred by Barry Geraghty’s grandfather – Laurence Geraghty


Arkle – 1964, 1965, 1966

Another household name to the older horse racing fans as Arkle become a firm favourite with punters after three Cheltenham Gold Cup wins between 1964 and 1966.

The last of those Gold Cups successes in 1966 saw him sent off at betting odds of just 1/10 – and in the process become the shortest-priced winner of the Cheltenham Gold Cup. A record he still holds today.

During his career, Arkle also landed other big races that included the Irish Grand National, King George VI Chase and Hennessy Gold Cup, but it was the Gold Cup – with three wins in – that he’s most famous for.

When he retired, Arkle ended with a race record of 27 wins from 35 starts (77% winning strike-rate)


Did you know? Two pints of Guinness were added to Arkle’s regular feed of oats each day



Desert Orchid – 1989

Okay, Dessie was more famed for his four King George VI Chase wins between 1986 and 1990, but he also added a Cheltenham Gold Cup to his CV in 1989.

The popular grey grabbed his Gold Cup win in heavy ground that day beating a horse called Yahoo in a sustained battle up the Cheltenham Hill to reward favourite backers at odds of 5/2.

Desert Orchid picked up just over £63k for winning the 1989 Cheltenham Gold Cup, while during his 23-race career he amassed £402k in total prize money.

With 13 wins from 23 races he ended with a (56%) winning strike rate and only finished out of the first three four times.


Did you know? After Dessie died in November 2006, his death made headlines all around the world, while his ashes were buried at Kempton Park – the scene of his four King George wins.


Norton’s Coin – 1990


Okay, probably not one of the Cheltenham Gold Cup greats, but Norton’s Coin went into the Cheltenham Festival ‘hall of fame’ after winning the 1990 renewal at odds of 100/1!

He also broke the hearts of Desert Orchid fans that day, who was back in third at the 10/11 favourite and current Gold Cup champion at the time.

That 100/1 win still stands as the biggest-priced Cheltenham Gold Cup win in the race’s history.


Did you know? After winning the 1990 Gold Cup, Norton’s Coin raced 18 more times – but only won once more


Best Mate – 2022, 2003, 2004

The slightly younger horse racing fans will remember the three Cheltenham Gold Cup wins between 2002 and 2004 of Best Mate.

Best Mate was trained by Henrietta Knight and ridden by Jim Culloty in all three of those Gold Cup successes.

During his career he also added a King George VI Chase (2002) to his name and won 11 of this 16 races over fences.

In fact, Best Mate was placed in a remarkable 15 of his 16 chase races and the only defeat out of the first two places came in the 2005 Haldon Gold Cup at Exeter (pulled up), which sadly resulted in him collapsing and dying of a suspected heart attack soon after.


Did you know? Best Mate never fell over hurdles or fences during his career


Kauto Star – 2007, 2009

KAUTO STAR – This Paul Nicholls super star is another of the more recent Cheltenham Gold Cup greats – winning the race in 2007 and 2009, plus he also finished second in the 2008 renewal behind is stablemate at the time Denman.

Both Gold Cup wins saw him being sent off as favourite (5/4 and 7/4), while when he won his 2009 race he became the first ever horse to regain the Gold Cup – a record that still stands today.

During his racing career he won a massive £3.7m in total prize money and bonuses, winning 19 of his 35 races (54%).


Did you know? When Kauto Star retired in 2012 he was sent to train as part of the GB dressage team.


Denman – 2008

This beast of a horse was the main rival to Kauto Star with many racing fans in one camp or the others – likened to the modern day ‘Messi or Ronaldo’ debates in football.

In 2008, Denman got his rewards for some epic battles when winning the Cheltenham Gold Cup – a performance to this day many believe was one of the greatest Gold Cup wins of all time.

He had his stablemate – Kauto Star – beaten 7 lengths back in second that day and it was one of those wins that you feel no horse (past or present) would have beaten him in. His jockey at the time, Sam Thomas backed that up saying “the best I am ever likely to ride – on his day no horse would beat him”

Kauto Star got his revenge on Denman in the 2009 Gold Cup with the places reversed. While from his remaining 10 career races since winning the Gold Cup, Denman won just once (2009 Hennessy) more.

During his career, he won 10 of his 19 chase starts and won just over £1.1k in total prize money.


Did you know? Denman’s nickname was ‘The Tank’


Al Boum Photo – 2019, 2020

The most recent two-time winner of the Cheltenham Gold Cup after wins in 2019 and 2020.

This Willie Mullins-trained horse will also be back for more in 2022 as he looks to join Kauto Star as the only horses to regain the Gold Cup after losing out to Minella Indo.

You’d probably say that Al Boum Photo isn’t quite in the league of the other horses in this feature, but it’s hard to ignore a two-time winner of the Gold Cup and he deserves the credit – you never know he might even add another win in his race to his name!


Did you know? When Al Boum Photo fell in the 2018 RSA Chase, his jockey Ruby Walsh broke a leg and had to miss the remainder of the Festival.


Recent Cheltenham Gold Cup Winners

  • 2021 – MINELLA INDO (9/1)
  • 2020 – AL BOUM PHOTO (10/3 fav)
  • 2019 – AL BOUM PHOTO (12/1)
  • 2018 – NATIVE RIVER (5/1)
  • 2017 – SIZING JOHN (7/1)
  • 2016 – DON COSSACK (9/4 fav)
  • 2015 – CONEYGREE (7/1)
  • 2014 – LORD WINDERMERE (20/1)
  • 2013 – BOBS WORTH (11/4 fav)
  • 2012 – SYNCHRONISED (8/1)
  • 2011 – LONG RUN (7/2 fav)
  • 2010 – IMPERIAL COMMANDER (7/1)
  • 2009 – KAUTO STAR (7/4 fav)
  • 2008 – DENMAN (9/4)
  • 2007 – KAUTO STAR (5/4 fav)
  • 2006 – WAR OF ATTRITION (15/2)
  • 2005 – KICKING KING (4/1 fav)
  • 2004 – BEST MATE (8/11 fav)
  • 2003 – BEST MATE (13/8 fav)

Cheltenham Gold Cup Betting Trends

  • 19/19 – Aged 9 or younger
  • 18/19 – Had raced within the last 3 months
  • 17/19 – Had run over fences at Cheltenham before
  • 16/19 – Finished 1st or 2nd last time out
  • 16/19 – Came from the top 3 in the betting
  • 16/19 – Had won over at least 3m (chase) before
  • 14/19 – Winning distance – 2 lengths or more
  • 14/19 – Won last time out
  • 13/19 – Placed favourites
  • 12/19 – Had won 5 or more times over fences in the UK or Ire before
  • 11/19 – Rated 170 or higher
  • 11/19 – Irish bred
  • 9/19 – Winning favourites
  • 8/19 – Had last raced in the previous calendar year
  • 8/19 – Had won over fences at Cheltenham before
  • 8/19 – Irish-trained winners (5 of the last 6)
  • 5/19 – Last race was in the King George VI Chase (Kempton)
  • 4/19 – Won the Denman Chase (Newbury) last time out
  • 3/19 – Trained by Paul Nicholls
  • 2/19 – Ran in the Savills Chase last time out
  • 2/19 – Trained by Nicky Henderson
  • 2/19 – Trained by Willie Mullins (2 of the last 3)
  • The average winning SP in the last 18 renewals is 11/2

Other Cheltenham Gold Cup Stats

  • Only one horse (Kauto Star 2009) has ever regained the race
  • 27 of the last 28 winners have been aged 9 or younger
  • 9 of the last 20 winners came here fresh – did not race that same calendar year
  • 17 of the last 21 winners were rated 166 or higher
  • 21 of the last 23 winners had won a race already that current season
  • 15 of the last 21 winners had finished second or better at the Cheltenham Festival before
  • 11 of the last 22 winners had run in that season’s King George VI Chase (Kempton)
  • 21 of the last 22 winners had won a Grade One Chase contest before
  • The last winner aged older than 10 was in 1969 (What a Myth, 12)
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