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Cheltenham Festival Memories: Six of the best Gold Cup races

We look back on six winners of the Gold Cup  

The Cheltenham Gold Cup has produced more than its fair share of memorable moments over the years. Who could forget Denman’s battles with Kauto Star? Or Best Mate landing a hat-trick of pots from 2002 to 2004?

From Dawn Run to Lord Windermere, we’ve looked back at six of the best Cheltenham Gold Cup winners.

2014 – Lord Windermere
2011 – Long Run
2008 – Denman
2004 – Best Mate
1989 – Desert Orchid
1986 – Dawn Run

2014 – Lord Windermere

The closest Gold Cup since 1992 belongs to 2014 winner, Lord Windermere. The Oscar gelding enjoyed a pretty nomadic career prior to victory around Prestbury Park in March 2014.

He’d won a number of weak contests in Ireland alongside an impressive success in the RSA Chase. But his season leading up to his first and only Gold Cup win was strewn with disappointment. Soundly beaten in the Hennessy Gold Cup, Lexus Chase and the Irish Gold Cup, he rocked up at Cheltenham with a puncher’s chance at odds of 20/1.

After travelling poorly and hanging about towards the rear of the field, he kept in touch with the leading pack from four out and soon made his move. A switch to the outside with two to go put him on terms with Silviniaco Conti, Bobs Worth and Lyreen Legend, and just in front of God’s Own and the Giant Bolster.

Despite hanging badly to the right, Jim Culloty’s charge clung on to edge out God’s Own by a short-head and become the longest-price winner of the Gold Cup since Cool Dawn in 1998.

There was even more drama after the race, as Lord Windermere survived a steward’s enquiry to take the result. That victory proved to be his last ever win, with a subsequent tilt at the big pot resulting in the Oscar gelding being pulled up. His last run came at Punchestown in April 2018.

2011 – Long Run

Now veterans, Kauto Star and Denman returned for their sixth Cheltenham Festival on the bounce against new kid on the block, Long Run.

Since the 2008 encounter, Denman had suffered from heart problems and finished second twice more in the Gold Cup. He had produced one of the all-time great steeplechasing performances to land the 2009 Hennessy Gold Cup, too.

Rival Kauto Star had continued to rewrite the record books, including the scintillating Gold Cup win in 2009, before his horrific fall at the top of the hill in 2010.

The 2011 renewal provided as strong a field as ever, with the previous year’s winner Imperial Commander back to defend his crown. Midnight Chase led for the majority, but after falling away, it was left to Kauto Star, Denman, Imperial Commander and Long Run to battle it out up the front.

Imperial Commander cracked, and for a fleeting moment, it looked as though we were about to get the match racing fans had been waiting for since 2008, as Kauto Star and Denman went head-to-head.

However, the younger legs of Long Run soon told. He powered away past both Denman and Kauto Star, who both ran gallant races in defeat.

2008 – Denman

The rivalry between Denman and Kauto Star really captured the public’s imagination. The latter had won his first Gold Cup in 2007 while the former hacked up by over 10l to take the Royal and Sun Alliance Novices’ Chase in the same year.

That helped set-up a mouth-watering first-time clash between the two Paul Nicholls-trained horses in the 2008 Gold Cup.  Kauto Star was a slight doubt after returning lame from his prep-win at Ascot a month earlier, whilst Denman went in three from three after triumphing off top weight in the Hennessy Gold Cup.

Their battle did not disappoint. Indeed, the 2008 Gold Cup is considered one of the most thrilling in modern racing history. Denman, nicknamed The Tank, put his rival to the sword thanks to two rounds of incredible and precise jumping.

He had Kauto Star in trouble going down the hill before going clear four out and staying on well to take his one and only Gold Cup by an impressive 7l. Richard Hoiles’ commentary really helps capture the emotion of the day.

2004 – Best Mate

Not since Arkle in the 1960s had a horse completed a hat-trick of Gold Cup victories. Best Mate changed that.

Having promised so much earlier in his career, he confirmed himself as a top quality chaser in the 2002 Gold Cup when beating Commanche Court and 1999 winner See More Business for Henrietta Knight and Jim Culloty.

The following year he looked to have a major threat in Irish raider Beef Or Salmon. But his bid ended with a crunching fall at the third fence. Best Mate then completed a sterling round of jumping before quickening off the bend to take his second Gold cup in as many years.

That set up a legendary tilt at Arkle’s record in the 2004 renewal. And Best Mate did not disappoint. Knight’s charge jumped with his usual fluency up until three out where Paul Carberry and Harbour Light attempted to box Best Mate in behind long-time leader First Gold.

Culloty didn’t panic and sent his rival around them. His class shone two out when Best Mate took two lengths out of his rivals at a critical moment before keeping on up the hill and sending Cheltenham into raptures.

Sadly Best Mate never was able to go for a fourth win in the race, with a setback meaning he missed the 2005 Gold Cup before he tragically lost his life at Exeter later that year following a heart attack.

1989 – Desert Orchid

Known as the housewives’ favourite, Desert Orchid was some horse. His record remains almost untouchable, even with a disappointing effort in his first Cheltenham jaunt in the Champion Chase.

He soon put that right the following year, though. After prepping for the race with five wins from five over fences, David Elsworth’s runner almost had his Gold Cup bid scuppered by heavy and persistent rain.

Facing 12 rivals, he hated every step of the way yet still jumped with the usual flashiness. He was still there coming down to the third last where Ten Plus, who was going strongly, fell. That left Dessie and Yahoo disputing the lead.

Going to the second last, he looked beaten. But after digging deep and fighting back tenaciously up the hill, he repelled Yahoo’s advances to claim one of the most famous Gold Cup wins in history. Sir Peter O’Sullevan’s commentary lives long in the memory.

1986 – Dawn Run

Our last entry is possibly the greatest mare ever to race in National Hunt history. To this day, Dawn Run remains the only horse to win both the Champion Hurdle and the Gold Cup. In short, she had everything – speed, stamina and plenty of guts.

After beating all before her over hurdles, she then went chasing – with huge success. However, things didn’t get off to the perfect start. Her run in the Gold Cup trial at Cheltenham ended in failure when she unseated Tony Mullins at the final ditch.

Mullins subsequently lost the ride to Jonjo O’Neill and the rest as they say, is history. Her 1989 Gold Cup bid started with a bad error but she recovered swiftly to dispute the lead with Run And Skip.

Dawn Run, Run And Skip, Wayward Lad and 1985 winner Forgive And Forget all had chances going into the final stretch. And it was Wayward Lad who led them over the final fence. But Dawn Run found extra towards the finish to the delight of the packed stands.

There was a sad end to her career, however. She fell at Aintree on her next start at the first fence before winning a match race at Punchestown against 1986 Champion Chase winner Buck House.

Her final start of the campaign was in the French Champion Hurdle at Auteuil in Paris, where she fell and sadly died.

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