We all enjoy making some bets now and again on our favourite sports. It probably won’t make us rich, but hopefully it won’t clean us out either. Winning big often involves a big risk, and when it doesn’t pay off the consequences can be devastating.

Of course, it’s the bookies who usually come out on top, but it’s always interesting when there’s a big upset. If you want to have a flutter of your own, take a look at some of the best betting sites Canada, which you can find here. Just make sure you stay sensible, or your story could end up as another cautionary tale. Here are just a few of the biggest winners – and losers – in the history of sports betting.

Winner: Steve Whiteley

Steve Whitely was a heating engineer and occasional racegoer who attended a 2011 event at Exeter racecourse in the southwest of England, entering the venue on a free promotional ticket. While there he decided to participate in the Tote Jackpot, a parlay bet on the winners of six races. Whiteley spent just £2 and chose the names at random.

While other attendees spent hours poring over the race cards to predict their six winners, Whiteley had no system. The final race was won by a horse that had lost 28 consecutive races beforehand, and was ridden by an inexperienced female jockey who had as yet never won a race at this level. Whiteley walked away with a little over £1.45 million that day.

Loser: Steven Richards

Another Brit, this time with a rather less uplifting tale. The story starts happily enough, as Richards also found success with a parlay bet on twelve football matches. From just £10, the roofing contractor from Wales came away £38,970 better off. If he had stopped there, Mr Richards would have found himself in our winners list.

Unfortunately, he succumbed to a common gambling fallacy – the idea of a lucky streak. Patriotic Richards proceeded to bet £30,000 from his winnings on Wales beating Australia at rugby. Seems he should have stuck to football bets, as the Aussies won and Richards waved goodbye to most of the money less than a week after winning it.

Winner: Leigh Herbert

The 2015/16 season was a magical one for EPL team Leicester City and their fans. It was only their second season in the top flight since promotion, and they had finished the previous year mid-table. UK bookmakers were offering 5000/1 for the team to win the title, and a few people took the bet. Some of them cashed out early as Leicester played game after game of sublime football.

One fan who stuck to his guns was local man Leigh Herbert, who placed a £5 bet for a laugh while on holiday. Despite bookie William Hill trying to tempt him with an early payout, Herbert believed in his team and didn’t back down, eventually netting £20,600 for his faith when Leicester defied the odds to lift the winners’ trophy.

Loser: Michael Jordan

So far, we have kept this list about mere mortals, but in order to lose big you usually have to bet big, and that means celebrities. Nobody in their right mind could call the venerable Michael Jordan a loser, but he did have a reputation for some pretty wild gambling habits. Much has been written on the subject, although none of it seems to have done Jordan much harm.

One story that did the rounds was a $1.2 million loss to a businessman friend over some games of golf. According to Richard Esquinas, the two played over ten days and wagered thousands on each swing of the club. The story may not be entirely true, although it helped Esquinas to sell his book back in the 1990s. Whatever the truth of the matter, Jordan himself is doing just fine, with a net worth estimated at $1.6 billion US.