Harry Redknapp Horses at the Cheltenham Festival
Harry Redknapp is famous for being a football manager and has worked with top clubs such as Tottenham, West Ham, Portsmouth, and Southampton. However, he has also made a name for himself in horse racing by owning several successful horses over the years.
Within this page, you will gain insight into Redknapp’s background, notable achievements, and the horses he owns competing in the upcoming Cheltenham Festival. The page also provides a detailed analysis of Redknapp's historical performance at the festival, offering bettors and enthusiasts valuable information.
An Introduction to Harry Redknapp and His Horses
Redknapp has had a few successful runners at Cheltenham in the past and enjoyed his first festival win in 2024 with Shakem Up’Arry. His venture into horse ownership has brought an added layer of excitement to major events like the Cheltenham Festival.
His horses often attract attention due to their impressive pedigree and performances. Collaborating with respected trainers and investing in quality bloodlines, Redknapp has seen notable successes in other prestigious races, further cementing his credibility in the racing community.
Despite this, Redknapp saw little success in 2025, with just two runners throughout the festival. Most notably, one run came in the TrustATrader Plate on 13 March, which saw Shakem Up’Arry finish 14th of 20. Another of Redknapp's horses, The Jukebox Man, looked to be a contender but was ruled out for the season with an injury in late January 2025.
Harry Redknapp at Cheltenham Festival: The Key Highlights
Redknapp’s biggest win as a horse owner came at the 2024 Cheltenham Festival when Shakem Up’Arry, trained by Ben Pauling, triumphed in the TrustATrader Plate Handicap Chase. He also came close with The Jukebox Man in the Albert Bartlett Novices’ Hurdle in 2024, finishing second.
Horses Owned by Harry Redknapp Competing at Cheltenham Festival
The Jukebox Man
The Jukebox Man was expected to be a strong contender for the Brown Advisory Novices' Chase but missed the 2025 Cheltenham Festival due to injury. Redknapp will be hoping he can make a return in 2026.
| Category | Details |
|---|---|
| Horse Name | The Jukebox Man |
| Trainer | Ben Pauling |
| Jockey | Ben Jones |
| Scheduled Races | Cheltenham Gold Cup |
| Form | 2-2-1-1-1-1 |
Shakem’Up Arry
| Category | Details |
|---|---|
| Horse Name | Shakem’Up Arry |
| Trainer | Ben Pauling |
| Jockey | Callum Pritchard or Ben Jones |
| Scheduled Races | N/A |
| Form | 1-17-F-5-14-PU |
Fascinating Lips
| Category | Details |
|---|---|
| Horse Name | Fascinating Lips |
| Trainer | Gary and Josh Moore |
| Jockey | TBC |
| Scheduled Races | N/A |
| Form | 1-6-4-4-4-5 |
Yellow Car
| Category | Details |
|---|---|
| Horse Name | Yellow Car |
| Trainer | D Killahena & G McPherson |
| Jockey | TBC |
| Scheduled Races | TBC |
| Form | 2-1-5-3-1-4 |
Notable Horses from Harry Redknapp's History
Shakem Up’Arry
The 11-year-old gelding secured Redknapp his first win at the Cheltenham Festival in 2024.
Notable runs:
- March 2024, Cheltenham – 1st
- January 2024, Cheltenham – 1st
- March 2023, Cheltenham – 3rd
- December 2022, Exeter – 1st
The Jukebox Man
Notable runs:
- December 2024, Kempton – 1st
- November 2024, Newbury – 1st
- April 2024, Aintree – 2nd
Wake Up Harry
Wake Up Harry has three wins in 20 runs across his career.
Notable runs:
- July 2024, Newmarket – 2nd
- June 2024, Wolverhampton – 2nd
- April 2024, Chelmsford City – 2nd
Moviesta
Notable runs:
- July 2017, Dundalk – 1st
- October 2016, Dundalk – 2nd
- August 2016, Dundalk – 1st
Harry Redknapp's Performance at Cheltenham Festival
Redknapp has only managed one win at the Cheltenham Festival with Shakem Up’Arry in 2024. His success has been recent, but he hopes to build on that in the future.
Here are some key stats from Redknapp’s performances at the Cheltenham Festival:
| Year | Total Runs | Total Wins | Win % | Placed | Earnings |
|---|---|---|---|---|---|
| 2025 | 2 | 0 | 0% | 0 | N/A |
| 2024 | 3 | 1 | 33.33% | 1 | £96,144 |
| 2023 | 3 | 0 | 0% | 2 | £2,535 |
| 2022 | 0 | 0 | 0% | 0 | £0 |
| 2021 | 2 | 0 | 0% | 1 | £0 |
| 2020 | 1 | 0 | 0% | 0 | £0 |
| 2019 | 0 | 0 | 0% | 0 | £0 |
As you can see, Redknapp’s most successful year at the Cheltenham Festival was in 2024 by far, as he earned over £67,000 in winnings with one win and one place. This gave him a total win percentage of 33.33%. After a disappointing 2025 festival, he will be hoping for much more success at Prestbury Park in 2026.
Harry Redknapp at Cheltenham Festival 2024
Redknapp’s most notable year at the Cheltenham Festival has to be 2024 where he got his maiden win with Shakem Up’Arry. He also secured the most amount in earnings he has ever won, with a total of £96,144.
Speaking after the win, Redknapp explained what led to him naming the horse as he did: “I named him after a guy who used to stand behind me when I managed West Ham, and for 90 minutes, he’d shout: ‘Shake ’em up, ’Arry.” He also likened the Cheltenham Festival to “the Champions League of racing” and said that “to have a winner at Cheltenham is a dream.”
For the rest of the 2024 Cheltenham Festival, Redknapp also saw success with The Jukebox Man, who placed in the Albert Bartlett Novices' Hurdle. Having started the race at 18/1, he managed to finish 2nd behind Stellar Story in a photo finish, who was a huge outsider at 119/1.
The result meant Redknapp earned another £28,620 in prize money, but would’ve won £50,000 more had he managed to stay ahead at the last. Despite this unfortunate result, Redknapp was still delighted with his horse’s performance, saying, “What a run though wasn’t it? It was a great run. We’ve got a nice horse there.”
