If you’ve ever fancied yourself a bit of a fortune-teller, or you’re the sort who likes to back the underdog just for the thrill, then the Grand National is your kind of race.
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Every year at Aintree, dreams are dashed, legends are made, and—just occasionally—the punters are left scratching their heads as a betting slips), and let’s take a friendly canter through the tales of the Grand National’s most unlikely winners.
Tipperary Tim (1928): “You’ll Only Win If All the Others Fall!”
Let’s wind the clock back to 1928. Picture it: the Roaring Twenties, flapper dresses, jazz, and at Aintree, a field of 42 horses thundering towards the first fence. Among them, Tipperary Tim, a horse so unfancied that even his own connections probably didn’t bother to iron their best suits for jockey, Bill Dutton, was told by a friend before the race, “Billy boy, you’ll only win if all the others fall!” Well, sometimes fate has a sense of humour.
That year’s race was chaos on four legs. Fog, heavy ground, and a pile-up at the Canal Turn saw horse after horse tumble or pull up. In the end, only two finished: Tipperary Tim, who’d kept out of trouble at the back, and Billy Barton, who fell at the last but was remounted. Tipperary Tim trotted home, probably as surprised as anyone. If you’d had a tenner on him, you’d have been the toast of the pub for the next decade.
Gregalach (1929): Lightning Strikes Twice
You’d think the racing gods would’ve had their fill of surprises after 1928, but no. The very next year, Gregalach, another 100/1 shot, pulled off the impossible. This race boasted the biggest field in Grand National history: 66 runners. That’s more horses than you’d find at a pony club rally, and almost as much mayhem.
Gregalach, ridden by Robert W. H. Everett, managed to avoid the carnage as 57 horses failed to finish. Only nine crossed the line, and most of them were outsiders too. It was as if the favourites had read the script and decided to stage a mass protest. Gregalach’s win made it back-to-back 100/1 winners—something that’s never happened since. If you’d backed both, you’d have been able to buy your own racehorse, or at least a very nice hat.
Caughoo (1947): The Fog, the Fisticuffs, and the Fifty-Pound Wonder
Fast forward to 1947, and the Grand National was run in a fog so thick you’d have struggled to find your own horse, let alone the finish line. Enter Caughoo, an Irish outsider bought for just £50—a bargain even in those days. Ridden by Eddie Dempsey, Caughoo was so unfancied that conspiracy theories swirled after his win. Some claimed he’d missed half the fences in the fog, finishing as fresh as a daisy while others looked like they’d run the London Marathon in wellies.
The drama didn’t end at the winning post. There were heated words and even fisticuffs in the weighing room, but the result stood. Caughoo’s owner, John McDowell, probably never made a better investment. If you like your racing stories with a hint of mystery, Caughoo’s your horse.
Foinavon (1967): Right Place, Right Time, Right Price
If you’ve ever felt like you’re always in the wrong place at the wrong time, Foinavon’s story might give you hope. In 1967, he lined up at 100/1, with not much expected except a nice day out and perhaps a carrot or two. But at the 23rd fence, disaster struck: a loose horse caused a massive pile-up, with horses and jockeys scattered like confetti at a wedding. Foinavon, way behind, trotted up to the chaos, picked his way through the carnage, and jumped the fence as if out for a Sunday hack.
By the time the others had remounted and set off in pursuit, Foinavon was long gone. He won by a country mile, and the fence was later named after him—a rare honour for a horse who’d probably have been happy with a sugar lump and a pat on the neck.
Mon Mome (2009): The Modern Miracle
After Foinavon, it seemed the days of 100/1 winners were over. Then, in 2009, Mon Mome—French-bred, trained by Venetia Williams, and ridden by the late, much-loved Liam Treadwell—rocked the racing world. Mon Mome had been a decent horse, even favourite for the Welsh National not long before, but he’d drifted in the betting and was all but ignored by punters on the day.
But Mon Mome had other ideas. As the race unfolded, he stayed out of trouble, jumped beautifully, and when the leaders tired, he swept past to win by 12 lengths. Williams became only the second female trainer to win the race, and Treadwell’s beaming smile lit up Aintree. It was a fairytale for everyone—except the bookies, who probably needed a lie down.
What Makes a 100/1 Winner?
So, what do these five have in common, apart from giving bookmakers heart palpitations? Luck, for sure—sometimes a lot of it. But also grit, determination, and a knack for being in the right place at the right time (or, in Foinavon’s case, the very, very right time). The Grand National is a race where anything can happen—and, as these stories show, sometimes it really does.
And here’s the twist: although we like to think that bookies lose sleep over these shock wins, the truth is they often do just fine. Most punters back the favourites or go with well-known names, so when a complete outsider wins, the payout may be big—but only to a small number of people. The bookies still keep most of the money, especially when the popular horses fall by the wayside.
If you’re ever tempted to throw a couple of quid at a rank outsider, : it’s happened before, and it’ll probably happen again. Just don’t blame me if your horse is last by a furlong and stops for a snack at the water jump. That’s the Grand National for you—a glorious, unpredictable, utterly lovable lottery.
So, next time you’re at the bookies or watching the National with friends, raise a glass to Tipperary Tim, Gregalach, Caughoo, Foinavon, and Mon Mome. They’re proof that, in racing as in life, sometimes the long shots come good. And if you ever hear someone say, “You’ll only win if all the others fall,” just smile and say, “Stranger things have happened at Aintree.”
