Jockeys with the Most Grand National Wins

For every jump jockey, winning the Grand National is the ultimate ambition. It's the race every rider dreams about from the moment they first sit on a horse. To guide a runner safely around Aintree Racecourse, clear 30 famous fences, handle the pressure of a huge field and still have enough left for the run-in is one of the hardest tasks in sport.

Winning it once is enough to secure a place in racing history; winning it more than once turns a jockey into a legend.

Only a select group of riders in Grand National history have managed to win the race multiple times and even fewer have claimed three victories or more. Some of these names came from the early days of the race in the 1800s, while others are modern stars who produced unforgettable moments in front of millions of viewers.

Steering a horse to victory in the National takes more than just talent. It requires stamina, patience, tactical awareness, bravery and often a huge slice of luck. Even the very best jockeys can fall victim to the nationals most famous fences like Becher’s Brook, The Chair or the chaos of Canal Turn.

So who are the most successful Grand National jockeys of all time and what made them so effective over racing’s most famous course?

Why Winning the Grand National Multiple Times Is So Difficult

Before looking at the biggest names, it's worth understanding why repeat Grand National winners are held in such high regard.

First, simply getting a ride in the race is difficult.

To be trusted with a Grand National runner, a jockey must already be performing at the top level of National Hunt racing. Trainers are not willing to gamble on inexperience in a race where one mistake can end months of preparation. Riders need strong chasing records, stamina and the confidence to handle extreme pressure.

Then comes the physical challenge.

The Grand National is run over more than four miles and usually lasts around nine minutes longer than a standard top-class chase. Jockeys are in a crouched position for the entire race, balancing at speed while guiding a horse over huge fences and through heavy traffic.

There are 30 fences to jump, many of them unlike anything seen elsewhere in British racing. Becher’s Brook punishes poor landings. The Chair demands bravery and perfect timing. Canal Turn forces horses to make a sudden sharp left turn immediately after landing.

Mentally, it's just as demanding.

Push too hard too early and the horse may have nothing left for the final circuit. Hold on too long and the leaders disappear. Jockeys need to judge pace perfectly, avoid trouble and stay calm when chaos unfolds around them.

Amateur riders have occasionally won, with names like Marcus Armytage and Sam Waley-Cohen proving it can happen but in most years, experience is the deciding factor.

That is why multiple winners are so respected. Success at Aintree is never accidental.

George Stevens – Five Wins

When discussing Grand National history, one name stands above all others.

George Stevens remains the most successful jockey the race has ever seen, with an incredible five victories between 1856 and 1870.

His wins came aboard Freetrader, Emblem, Scawthorpe and twice on The Colonel. No rider since has managed to equal that total, despite more than 150 years of attempts.

Racing during Stevens’ era looked very different to the modern National. The course itself was rougher, the fences were less refined and wealthy spectators sometimes rode alongside the race on horseback to watch the action unfold. It was a far less controlled spectacle than the polished event we know today.

Stevens was known for being calm, quiet and incredibly level-headed. While others panicked in the chaos, he remained composed. That temperament made him perfectly suited to the unpredictable nature of Aintree.

His most famous victories came with The Colonel in 1869 and 1870, when he secured back-to-back wins and cemented his place in racing folklore.

He died young, at just 38, following a riding accident in bad weather near Cheltenham but his record has never been broken.

Five Grand National wins remains one of racing’s greatest achievements.

Brian Fletcher – Three Wins

Few jockeys are as closely linked to a single horse as Brian Fletcher is with Red Rum.

While Red Rum became the greatest Grand National horse of all time, Fletcher played a major role in building that legend.

His first National win actually came before Red Rum entered the picture. In 1968, he guided Red Alligator to victory as a young jockey from County Durham, announcing himself on the biggest stage.

Five years later came the moment that defined his career.

In 1973, Fletcher partnered Red Rum against Crisp in what became one of the most famous finishes in racing history. Crisp looked certain to win after jumping the final fence with a huge lead but Red Rum kept coming. Fletcher judged the finish perfectly, pushing his horse relentlessly to catch Crisp close to the line.

It remains one of the greatest Grand National moments ever seen.

He followed that success with another victory in 1974, steering Red Rum to back-to-back wins despite carrying the maximum weight of 12 stone.

Fellow jockey Peter Scudamore later called Fletcher the “unsung hero” of Red Rum’s story. His quiet personality and humble nature meant he often stood in the background while the horse took centre stage.

But those who understand racing know how important his rides were.

Tom Olliver – Three Wins

Tom Olliver was one of the earliest stars of the Grand National and one of Victorian racing’s most colourful characters.

He won the National in 1842 and 1843 before adding a third success in 1853 aboard Peter Simple, a horse he also trained himself.

That trainer-jockey combination was more common in the 1800s than it is today but it still demanded exceptional knowledge and skill. Preparing the horse and then delivering on race day required total confidence in both horse and rider.

Olliver also rode in the very first official Grand National in 1839, finishing second on Seventy-Four and went on to compete in a record 19 Nationals overall.

That level of longevity was remarkable, especially in an era when racing conditions were far tougher and far less forgiving.

He later became a pub landlord before returning to training later in life, adding another chapter to an already colourful career.

His influence on Aintree remains enormous.

Arthur Nightingall – Three Wins

Arthur Nightingall secured Grand National victories in 1890, 1894 and 1901, building a reputation as one of the most dependable riders of his era.

His first win came on Ilex, followed by another aboard Why Not four years later.

But it was his third victory that became truly memorable.

In 1901, Aintree was battered by snow, creating some of the worst conditions ever seen for the race. Heavy drifts covered parts of the course and the going was brutal, turning the National into a slow and exhausting battle of survival.

Riding Grudon, Nightingall stayed relaxed while others struggled.

Legend says he even chatted casually to fellow jockey Algy Anthony during the race before saying, “I must push on a trifle faster,” and pulling clear to win by four lengths.

Whether every detail of the story is true or not, it perfectly captures the confidence and calmness that made him such a successful National jockey.

Tommy Beasley – Three Wins

Tommy Beasley proved himself one of the most versatile riders of his generation by winning the Grand National three times and later enjoying major success on the flat.

His first National victories came in consecutive years, winning with Empress in 1880 and Woodbrook in 1881. Both victories showed his skill at managing lighter-weighted runners and making the most of tactical opportunities.

He added a third win in 1889 aboard Frigate, proving he could succeed under very different race conditions and against stronger competition.

What made Beasley especially impressive was his adaptability.

Many steeplechase riders struggled when switching disciplines but Beasley also became a top flat jockey and won the Irish Derby three times.

That balance of skill across different types of racing helped make him one of the standout riders of the era.

Tommy Pickernell – Three Wins

Tommy Pickernell, who often rode under the name “Mr Thomas,” enjoyed one of the longest and most unusual Grand National careers in history.

He rode in 17 Nationals and won three of them across a 15-year period.

His first success came in 1860 aboard Anatis. According to racing folklore, a rival jockey supposedly offered him a bribe during the race to throw it. Pickernell refused and went on to win, adding even more drama to the story.

He followed that with another victory on The Lamb in 1871 and then won again in 1875 with Pathfinder.

There is also a famous tale that he was drunk during the Pathfinder victory and that the horse practically carried him around the course. Whether true or exaggerated, it became part of Grand National mythology.

His career shows just how much folklore surrounds Aintree’s greatest names.

Jack Anthony – Three Wins

Jack Anthony claimed three Grand National wins in just nine years and established himself as one of the leading riders of the early 20th century.

His first success came in 1911 aboard Glenside in terrible weather conditions where only four horses managed to finish.

In 1915, he won again on Ally Sloper, creating history by delivering the first female-owned Grand National winner for Lady Margaret Nelson.

His third triumph came in 1920 when he steered Troytown to a dominant 12-length victory.

Anthony wasn't just an Aintree specialist. He also won the Cheltenham Gold Cup twice, proving himself across the very highest level of jump racing.

That consistency across major races helped confirm his place among the sport’s elite.

Leighton Aspell – Two Wins

Not many jockeys win back-to-back Grand Nationals and even fewer do it on different horses.

Leighton Aspell achieved exactly that.

After waiting more than two decades for his first National success, he finally broke through in 2014 aboard Pineau De Re, a 25/1 outsider who won by five lengths.

Twelve months later, he returned and did it again with Many Clouds, another 25/1 shot, defeating Saint Are in a dramatic finish.

Back-to-back wins in such an unpredictable race are exceptionally rare and highlighted Aspell’s patience and tactical intelligence.

He retired in 2020 with more than 900 career wins and a reputation as one of the modern National’s coolest operators.

Davy Russell – Two Wins

Davy Russell’s two Grand National victories came aboard one of the most loved horses of modern jump racing, Tiger Roll.

He won in 2018 and 2019, helping Tiger Roll become the first horse since Red Rum to win back-to-back Nationals.

Russell was known for his patience and race management. Rather than forcing his horse into the race too early, he trusted Tiger Roll’s stamina and jumping ability, allowing him to travel comfortably before making his move late.

That calm approach made him the perfect partner for such a popular and talented horse.

Russell later retired after a glittering career that included multiple championship titles and major Cheltenham victories but those two National wins remain career-defining moments.

Ruby Walsh – Two Wins

Ruby Walsh was already a rising star when he won his first Grand National in 2000 but that victory helped turn him into a household name.

At just 20 years old, he guided Papillon, trained by his father Ted Walsh, to victory in a result that surprised many.

Five years later he returned with a much bigger reputation and delivered again, winning aboard Hedgehunter in dominant style.

That second victory showed the difference experience can make. Walsh controlled the race with confidence, producing one of the smoothest rides seen in the modern National.

Across his career, he became one of jump racing’s most decorated jockeys, winning multiple championship titles and countless festival races.

His success at Aintree was just one part of an extraordinary career.

Richard Dunwoody – Two Wins

Richard Dunwoody was one of the most reliable Grand National jockeys of his generation and a rider many punters loved to back.

He won his first National at just 22 aboard West Tip, carrying one of the highest weights in the field and proving his class early.

His second victory came in 1994 with Miinnehoma, a 16/1 outsider who outran expectations.

What made Dunwoody especially respected was his consistency. He rode in 14 Grand Nationals and placed on eight occasions, making him one of the safest each-way jockeys for bettors to follow.

West Tip alone ran in six consecutive Nationals, with Dunwoody regularly producing strong finishes.

Alongside his National success, he also won major races like the King George VI Chase and multiple British jump jockey championships.

Other Jockeys with Two Wins

• Chris Green – 2 Wins (1850, 1959)
• Alec Goodman – 2 Wins (1852, 1866)
• John Page – 2 Wins (1867, 1872)
• J. M. Richardson – 2 Wins (1873, 1874)
• Ted Wilson – 2 Wins (1884, 1885)
• Percy Woodland – 2 Wins (1903, 1913)
• Ernie Piggott – 2 Wins (1912, 1919)
• Arthur Thompson – 2 Wins (1948, 1952)
• Bryan Marshall – 2 Wins (1953, 1954)
• Pat Taaffe – 2 Wins (1955, 1970)
• Fred Winter – 2 Wins (1957, 1962)
• Carl Llewellyn – 2 Wins (1992, 1998)
• Derek Fox – 2 Wins (2017, 2023)

What Makes a Grand National Winning Jockey?

Winning the Grand National is never just about bravery. It's about control.

Physically, jockeys need to stay balanced and sharp for more than four miles, jumping 30 fences while managing a horse that may be tiring underneath them.

Mentally, they need discipline and trust.

Race plans matter but flexibility matters even more. A loose horse, a poor landing or bunching at a fence can change everything in seconds. Great jockeys stay calm while others panic.

They also need a strong relationship with their horse. Understanding when to settle, when to ask for more and when to conserve energy can decide the race.

Even then, luck plays a huge part.

The best riders maximise the things they can control and hope the rest falls their way.

How Grand National Success Influences Betting

When horse racing bettors study Grand National betting, many focus first on the horse, its form, the trainer or the weight it carries.

But the jockey matters just as much.

An experienced rider with proven stamina and strong chasing form can significantly improve a horse’s chances. Jockeys who perform well in long-distance races throughout the jumps season, especially at meetings like Cheltenham, are often worth following.

Those who excel in races like the National Hunt Chase or the Cross Country Chase usually have the patience and judgement needed for Aintree.

Top jockeys also affect the horse racing betting market directly. Trainers trust them with their strongest runners, meaning they are often partnered with the favourites.

However, value can also be found with underrated riders who quietly keep producing place finishes without attracting huge attention.

Looking at jockey form alongside the horse’s profile gives a much clearer picture before placing a bet.

In the Grand National, the Wright choice is rarely based on one factor alone. The right jockey can be just as important as the right horse.