If the pinnacle for a footballer is to lift the World Cup, and the most magical moment for a golfer is to sink the winning putt in The Masters, for a jump jockey the career aspiration must surely be to pilot the champion horse home in the Cheltenham Gold Cup.
That race acts as the headliner towards the end of four days of high quality action at the premier jumps meeting, and if you ask any jockey it is on this hallowed Prestbury Park turf that he or she wants to thrive more than any other.
The horses may do the bulk of the grunt work but without a quality jockey on board they are unlikely to have much success, and that is evident in the fact that the best riders tend to get the plum jobs in the saddle.
Indeed, this is a concept that has been a fantastic helping hand for Cheltenham Festival punters. Backing the likes of Ruby Walsh and Anthony McCoy in the modern era, and legends of the sport from yesteryear such as Pat Taaffe and Peter Scudamore, has proven to be as smart a strategy as any.
To help punters bet smart in the future, or perhaps just as a useful resource, we thought we’d publish a guide to the most successful jockeys in the history of the Cheltenham Festival.
Jockeys with the Most Wins
Given that the Cheltenham Festival dates back to the 1860s, there has been ample opportunity for the best jockeys in the business to get a healthy number of winners under their belts.
The great and the good have all contested the event’s biggest races, and you can rest assured that the list of the winning-most jockeys in Cheltenham Festival history features the finest handlers ever to slip into those figure-hugging silks.
As of the end of the 2023 edition of the meeting, these are the top 10 jockeys of all time as far as Cheltenham Festival winners are concerned.
Cheltenham Festival All Time Leading Jockeys
| Rank | Jockey | Wins |
|---|---|---|
| 1 | Ruby Walsh | 59 |
| 2 | Barry Geraghty | 43 |
| 3 | Anthony McCoy | 31 |
| 4 | Paul Townend | 28 |
| =5 | Pat Taaffe | 25 |
| =5 | Davy Russell | 25 |
| 7 | Richard Johnson | 23 |
| 8 | Richard Dunwoody | 18 |
| =9 | Charlie Swan | 17 |
| =9 | Fred Winter | 17 |
| =10 | Robert Thornton | 16 |
| =10 | Tommy Carberry | 16 |
As you will have probably noted, a large number of these jockeys are from the modern era – that is no coincidence, given that five extra races were added to the Cheltenham Festival schedule as of 2005. More races means more chance to rack up some winners.
Some readers may be surprised to see that A.P. McCoy isn’t the leading jockey at the Festival, but it’s true that Ruby Walsh and fellow Irishman Barry Geraghty have dominated the undulating Prestbury Park track more than any other rider.
And remember, it’s no coincidence that the best jockeys get given the plum rides – it kind of goes without saying.
The Festival’s Leading Jockey Award
Named after the great man himself, the winner of the leading jockey prize at the Cheltenham Festival is handed the Ruby Walsh Trophy.
The leading jockey at each edition of the meeting is the one that has claimed more wins than any other – if two or more are tied, then the number of place finishes is also taken into account.
While the concept of the Cheltenham Festival leading jockey award has been around for a while, it was only in 1980 when it was formalised with a trophy for the first time. It was renamed after the great Ruby Walsh in time for the 2020 edition.
Here’s a rundown of the most prolific winners of the leading jockey award at the Cheltenham Festival.
Cheltenham Festival Leading Jockey Awards
| Rank | Jockey | Awards |
|---|---|---|
| 1 | Ruby Walsh | 11-time champion |
| =2 | Peter Scudamore | 3-time champion |
| =2 | Paul Townend | 3-time champion |
| =3 | Jonjo O’Neill | 2-time champion |
| =3 | Charlie Swan | 2-time champion |
| =3 | Richard Dunwoody | 2-time champion |
| =3 | Anthony McCoy | 2-time champion |
| =3 | Mick Fitzgerald | 2-time champion |
| =3 | Barry Geraghty | 2-time champion |
There have been plenty of jockeys that have taken the top award on a single occasion, but this is the full list of multiple-time champions as of 2023.
As you can see, Ruby Walsh’s partnership with Willie Mullins – among other top trainers – has proven to be very fruitful indeed, and that is why he has left the likes of Scudamore and McCoy in his dust as far as this competition is concerned. You can certainly see why the trophy has been named after him!
Can You Bet On the Cheltenham Festival Leading Jockey?
The popularity of the Cheltenham Festival means that bookies are only too willing to take bets on all manner of markets, not just on individual races.
And that includes several categories relating to jockeys, from picking the leading jockey each day, whether Irish or UK jockeys will capture the most victories and, of course, the identity of the winner of the Ruby Walsh Trophy.
If you can align yourself to the right trainer and horses, this is a betting market that can prove very fruitful indeed!