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West Ham legend Harry Redknapp’s star signing eyeing up Cheltenham Gold Cup success

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West Ham United stormed past Brentford in an emphatic penalty shoot-out win in the FA Cup fifth-round, but former boss Harry Redknapp is eyeing up a different kind of silverware with the Cheltenham Gold Cup looming.

The annual festival begins today and runs until March 13th.

And West Ham United legend Harry Redknapp most certainly has a dog in the fight. Well, a horse in the race.

We win it on pens 😎 Do you fancy us to beat Leeds and book a trip to Wembley?!

A graphic showing the full-time score between West Ham United and Brentford (2-2, 5-3 pens) in the FA Cup on 09/03/2026.
Credit: Getty Images/Ben STANSALL / AFP

After Alphonse Areola made a donkey out of Dango Ouattara at the London Stadium, Redknapp is hoping to get a tune out of The Jukebox Man in this Friday’s Gold Cup.

West Ham United legend Harry Redknapp eyeing Gold Cup glory

Redknapp, now 79, partnered with highly-rated trainer Ben Pauling seven years ago. A partnership which both men hope will be marked by The Jukebox Man, a £70,000 purchase, becoming Gold Cup champion amid an era of Irish-trained domination.

The eight-year old bay gelding triumphed at the Ladbrokes King George VI Chase at Kempton Park on Boxing Day. As a result, expectations are high for The Jukebox Man in Cheltenham.

Race horse owner Harry Redknapp (L), trainer Ben Pauling (R) and Jockey Ben Jones pose with Cheltenham Festival hopeful The Jukebox Man at the Ben Pauling Stables on the Naunton Downs Estate, near Cheltenham, western England, on February 23, 2026. (Photo by Darren Staples / AFP via Getty Images)
Photo by Darren Staples / AFP via Getty Images

“That’s a dream and to have a horse that good is unbelievable,” Redknapp said that day, via ESPN. “I love the game. To come here on King George day and just run made me so proud, but to have the winner is special.

“What a race he has run and he jumped unbelievably. When they came to him, I thought he was beat and would finish fourth, but he’s come again and the guts the horse has shown is just amazing.”

Redknapp feels The Jukebox Man ‘has as good a chance as any’

“It’s a dream to have a horse to run in the Gold Cup and go there with a chance,” the former Portsmouth, Southampton and Tottenham coach told Racing TV in a much more recent interview.

West Ham eye FA Cup glory as Harry Redknapp goes for Gold! 🥇

Who are you backing for Cheltenham success? 🐎

Race horse owner Harry Redknapp watches Cheltenham Festival hopeful The Jukebox Man warm up at the Ben Pauling Stables on the Naunton Downs Estate, near Cheltenham, western England, on February 23, 2026.

“I’ve had an awful lot of horses, still got an awful lot, but this one has taken us to places that you only dream about as a racehorse owner. He’s my dream, he’s not for sale and he wouldn’t be for sale at any price.

“I’m not saying we’re going to win it but we’ve got a serious horse. It’s an open race and I think we’ve got as good a chance as anything.”

Approaching his 80th birthday, a return to Premier League management has been floated regularly in recent times, though Hammers News were told by a source close to the board that West Ham were not considering a Harry Redknapp reunion at a time when Nuno Espirito Santo was under severe pressure.

Redknapp is particularly pessimistic about Tottenham’s hopes of survival, meanwhile, at a time when two of his beloved old clubs are battling to avoid that final relegation spot.