Harry Redknapp refused to let Tottenham players attend Cheltenham – but ended up in box with squad after tempting offer

Harry Redknapp loves the racing and he’s eyeing glory at Cheltenham Festival this week.

In fact, so much is his love for Cheltenham that he was easily won over by his Tottenham squad when he was their manager.

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The 79-year-old footy legend, who owns many horses, tried his best to be a stern example while at Spurs in the early 2010s, after his players booked to attend the festival without his permission.

talkSPORT host Jamie O’Hara, who played under Redknapp, revealed that he refused to let them go at the time.

However, all it took was a clever offer from one of his teammates to convince Redknapp to make a complete U-turn on his stance.

Telling the hilarious story about his old boss, O’Hara said in 2021: “The first Cheltenham Festival I went to was when I was at Spurs.

“I went there with the Spurs squad where [teammates] Robbie Keane and Jonathan Woodgate [are] big on the races.

“We have a team bonding day and we went on our day off, which was the Wednesday, organised a chopper [to get there]…

“I remember getting to this abandoned airport and the chopper was in the middle of the airport and we’re all racing around in our Porsches and Bentleys.

“We went and had a great day…we’ve then come in on the Thursday and Woody has organised it again for a select few.

“And Harry Redknapp got wind of the fact we were going to Cheltenham on the Thursday as well…we had Man United on the Saturday.

“He pulled us all in at the start of the training session and said: ‘I’ve got wind that a load of you are going to Cheltenham again today, I’m not having it, you’re not going, don’t even think about it’.

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“We had the training session, everyone has gone back into the dressing room, Keano and that are saying: ‘What are we going to do?’

“Woody’s gone: ‘Give me five, I’ll go and have a chat with him.’

“I’ll never forget it – he’s gone in and said to Harry: ‘We’ve sorted it all out, we’ve got the chopper taking us there, we’re not going to go mad, it’s going to be a chilled one, not crazy, we’re all coming back straight after, in the cars, straight home.’

“Harry still wasn’t having it and Woody’s gone: ‘If I organise another chopper for you and your mates, do you want to come in the box?’

“Harry had a think about and went: ‘Yeah, I’ll have a bit of that!’

“So, straight after training, all of a sudden, Redknapp’s in the chopper and we’re all at Cheltenham on the Thursday, he’s sat in the box in with the hospitality….I was thinking, hold on a minute, he’s just said we’re not allowed to go and he’s in here with us!”

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Redknapp at Cheltenham

It was clear that you couldn’t keep Redknapp away from the Cheltenham Festival, even over a decade ago.

And now, one of his horses has gone on to win a race there.

Shakem Up’Arry won the Plate Handicap Chase in 2024 and Redknapp is now eyeing glory in the Gold Cup on Friday.

Jukebox Man is one of the favourites to win the biggest prize at the festival, coming up against Jango Baie and Gaelic Warrior.

A win in the Gold Cup has been something in Redknapp’s sights since the end of 2025, after Jukebox Man won the King George VI Chase at Kempton on Boxing Day.

Speaking in December about the Gold Cup, the ex-Tottenham manager told talkSPORT: “Well, that’s the target. That’s the dream.

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“Someone said the other day, you’ve just won the Champions League, and now we’re going into the World Cup for the Gold Cup.

“That is the quality of the race again. We certainly go there with a chance. So I’m looking forward to that in March.”

He added: “I love the racing. It’s my big passion. I’ve got a lot of horses and you dream about always having a good horse.

“I was lucky to go to Cheltenham and have a winner at the festival with Shake ‘em up Harry two years ago.

“Now Jukebox Man has taken me to the races I’ve always dreamed of going to. So it’s fantastic.

“The only trouble was, I took my wife racing the other day. She never goes and she thinks every meeting or every race is like that!”