September 20

Top 5 highest online casino wins in history

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META: Take a look at our picks for the highest online wins in casino history.

There is some great feeling in sharing in casino wins. People can feel the rising tension as the game progresses, only to let it all go when there is a winning return. And this is never more obvious than online, where the nature of sharing in a win is public for anyone in the world to see. For the best examples, take a look at our picks for the highest online wins in casino history.

Stoyan Madanzhiev breaks records at the WSOP

If you’re a fan of poker, no doubt you’ve been following the World Series of Poker every year as it turns Las Vegas upside down. If not, you might follow the WSOP tour, or even the European tournament. But few know of the WSOP Online Tournaments, which takes place every year alongside the WSOP in Vegas, where plenty of online players can compete for the biggest wins.

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One of these wins was Stoyan Madanzhiev, who broke records in his 2020 WSOP main event win, taking home a massive $3.9 million. That’s a serious upgrade from the $5,000 he entered with. He beat out 5,802 players, 38 of which appeared on the final day, to get that win.

You can have a similar experience for yourself, without the pressure of applying for a tournament and their steep admittance rates, by looking for a live dealer casino with a poker table. You can have the experience of sitting down at a poker table, having a friendly dealer deal you in, and play with all the other players at the table. It brings the poker table to your home with no effort.

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Drake’s on the high stakes

It’s hard to mention online casino wins without mentioning the man, the myth, the Canadian rapper and singer, Drake. That swing from music to casinos, without a lodge in Vegas, is noteworthy enough, but Drake has taken to playing at the slot machines – for an audience. His favourite is the roulette table, which, in a partnership with Stake, he regularly visits to get on with some gambling, with some 200,000 audience members watching via stream.

Now, this isn’t the first time Drake has got into the live streaming gig, but rarely did a round of Fortnite result in the rapper going home with $3 million, $5 million or even $25 million at one point.

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TrainwreckTV streams a $22.5 million win

And if you’re familiar with gaming streamers, chances are you’ve come across TrainwreckTV on Twitch. Initially known for offering his political opinion on stream, lately he’s turned to online slot machines for entertainment, where he and his captive audience watch the winnings come in.

Creator Tyler Faraz Nikham’s most notable win was on the Pragmatic Play slot, Might of Ra, where he won $22.5 million while streaming, making for a magic moment for creator and user alike.

Roshtein is a winning machine

But Trainwreck is not the first to make a career of streaming his slot wins. Right in front of him is Roshtein, who has so many winnings under his belt he might as well retire. His favourite slot machine is undoubtedly the Wanted Dead or a Wild slot. Famed for its high volatility, this paid off when it sent him winnings of $9 million, $16.6 million and peaked at $127.5 million all within six months.

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The many winners of the Absolutely Mad Million Mega Moolah

If you’re a fan of slots, it’s possible you’ve heard of the Absolutely Mad Million Mega Moolah. This safari-themed slot machine is known for creating some of the biggest online slot jackpot winners in history. With five reels and 243 paylines available, it’s hard not to win.

Some notable examples include British soldier Jon Heywood who bet 25p and won $20.1 million, Matawan gambler Rawiri Pou with a $10.1 million win, and Canadian “M.G.” who left the slot machine with $11.6 million in his pocket.


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Drake’s on the high stakes, Roshtein is a winning machine, Stoyan Madanzhiev breaks records at the WSOP, The many winners of the Absolutely Mad Million Mega Moolah, top 5 highest online casino wins in history, TrainwreckTV streams a $22.5 million win


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