10 Betting Experts Share Their Biggest Win (& How They Pulled It Off)

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Today we’ve decided to take a break from the usual posts of our online bookmaker reviews and how-to tips.In this article, we will bring you a list of betting experts sharing their biggest win in sports betting and more importantly; how the managed to pull it off.

In this round-up post we have for you below, you will learn about the many heartbreaks, upsets, six-figure wins and everything in between that is to be expected when you make sports betting your business.

There are many things that you can learn from in this post today, so we’d like to send a big thank you to all the experts who participated in this roundup.

We also urge you to follow through to their websites with the link provided for more tips, ideas and sports betting strategies.

We hope you enjoy this post and feel free to leave us a comment down below if you have any questions that you need answering from these 10 following betting experts.

Enjoy.

10 Betting Experts Share Their Biggest Win (& How They Pulled It Off)

Betting Experts Share Their Biggest Win

Marius Norheim – TradeMateSports.com

Thanks for reaching out. Happy to share a story, although mine will be slightly different.

I’m all about finding value, not trying to pick winners. So my goal is to find an edge, then get in a high volume of bets, which results in a steady profit growth.

Not risking a too large portion of my bankroll on any particular game.

What I would like to talk about is a Russian soccer game between Ural – Rostov. Norsk Tipping, the major Norwegian bookie, had Ural at 2.95 in odds to win, which was a 30% edge vs the Asian markets at the time. I got in at 2.6 with $100, still a 15% advantage.

The Asian market kept dropping due to Rostov resting a half of their first team.

I decided to hedge out by taking an Asian Handicap +0.5 on Rostov. Ensuring that I would be break-even on a draw or Rostov win and have an 11,7% sure bet given a Ural win.

Ural won 1-0. My initial bet closed at a 47.7% edge at the time the game started. I made a net profit of $60 but would have won $160 if I had stuck with my initial bet.

The lesson I learned is that hedging can reduce your risk, but it will also eat into your potential profits.


Jonas Gjelstad – TradeMateSports.com

Jonas Gjelstad, the founder of Trademate has an even better story. Besides being a very profitable sports bettor, Jonas is also a formidable poker player. In 2016 he won the Norwegian Heads Up Poker Championship. 

My largest win came in the 2014 soccer World Cup. Norsk Tipping, the major Norwegian bookie, offered 60 in odds on the Netherlands winning exactly 3-2 vs. Australia.

While the rest of the market was at 34-38 in odds, I put down $1000 and cashed out $60,000.

At this time I was living with Felix Stephensen, another Norwegian poker player.

Who also bet $1000 on the game. Felix spent a part of his winnings on a ticket to the WSOP where he ended up finishing second, cashing out $5,2 million in the main event.


Gavin Wood – BetCraft.co

My biggest win was during the 2011 World Cup.

The match was New Zealand vs. Japan, and I had wagered approximately £10k on New Zealand -70.5 and £9k on Japan +76.5 meaning that should New Zealand win by between 71-76 points, then both bets would win.

At 79 minutes New Zealand was leading by 69 which was almost good enough, but not quite.

With the last play of the game, Sonny Bill Williams scored his second try, which was then converted, leaving me as a very happy man!


Joseph Buchdahl – 12Xpert.co.uk

While I might be a betting analyst expert, this does not extend into the realm of prediction. Understanding how a betting market behaves is not at all the same thing as knowing how to find real positive expectation.

I’m good at the former, not so good at the latter. Yes, I can show people how to find positive expectation at soft books, but soon they will find themselves limited.

I don’t consider myself to be good enough to find positive expectation at the sharp books like Pinnacle. Many claim to be good enough, very, very few really are in practice.

Additionally, I’m rather against defining betting experts in the sense you are talking about, i.e. profitability, by their biggest win, since this measures their ability by an outcome when all my work tries to move people away from that idea.

Don’t study the outcomes to see if someone is any good at forecasting, study their forecasting process and see if that leads to a consistent profit.

Whilst you have asked for the method of how it was pulled off, basing this on just one big bet is still likely to bias conclusions.

I hope you can see where I’m coming from.

All that said, I suppose if you must have my biggest win, then here it is. It’s biggest in the sense of expected value, i.e. the size of the bookmaker’s mistake, and remains my favourite bet I have struck and won.

The occasion was 9th August 2003. UK bookmakers like to offer silly bets on the weather like snow on Christmas day and will we see a temperature above 100 Fahrenheit somewhere in the UK.

Typically, we get long odds for these sort of unlikely events. The latter in particular hadn’t ever happened, so typical odds were of the order of 10/1 and longer.

In that particular August leading up to the 9th, we’d had a few pretty hot days in the high 80s and low 90s and bookmakers had shortened odd of it happening to about 4/1.

Clearly, they were applying a strong favourite-longshot bias, guarding against the possibility of an extreme event, since even in hot summers we’re not like to get anywhere near 100F in the UK.

Well, at 11 am on the 9th I happened to be looking at the BBC weather forecast, and they were talking about a plume of unusually hot air that had crossed over from France. France already had a temperature of 38 Celsius (over 100 F), and London was already at 35C (95F).

For 11 am this was unusually hot, so I figured that strange meteorological event was taking place. I figured it was almost a certainty that parts of the south-east would get above 100F that day given the early heat and we still had about 4 to 5 hours until the maximum heat of the day is typically reached.

I figured the fair odds to be in the region of 1/4. I checked Ladbrokes and took their 4/1 which they had failed to update.

The bet proved to be a winner. Regarding profit £100), it wasn’t amazing (they wouldn’t let me have more than £25 although I’d have happily bet £1,000 on this) but regarding expected value, I was probably holding 400%!!! Ladbrokes had basically failed to keep up to date with the day’s weather.

I have one other favourite which held, even more, value, but sadly; I was too chicken to place the bet. The following text is taken from my first book.

“William Hill astonishingly offered 200/1 on Primoz Peterka, the back-in-form Slovenian ski jumper, to win the opening ski jumping World Cup competition of the 2002/03 season at Kuusamo, Finland, despite the fact that he had won the qualifying competition the night before, and had been double world champion in previous seasons.

The true odds, by contrast, were likely to be nearer to 10/1, and most other bookmakers had priced accordingly. Peterka won, and William Hill ceased offering odds for the ski jumping World Cup thereafter.”

I remember thinking about putting £10 down but thought 200/1 shots just don’t happen, no matter how large the mistake the bookmaker has made.

It taught me a valuable lesson by reminding me to bet on the value, not on what I think will happen.


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Roberto Cassini – Green All Over

My biggest win occurred on May 26,2011.

Miami Heat was playing an NBA play-off game in Chicago, and with four minutes remaining, trailed by nine points to the Bulls.

I decided to lay £30,000 at 1.03, risking £900. The bet was taken shortly afterwards, and the Bulls price dropped to 1.01 as the lead extended to 12.

I’d accepted the loss, but with 3:02 remaining the Heat, at that time starring LeBron James, Dwayne Wade and Chris Bosch, lived up to their name and got hot. Miami made up the deficit with one minute remaining, eventually winning by three points.


Path Hagerty – FishyFive.com

I won six figures a few years ago in an NFL suicide pool.

I give all the details in my book – Good Teams Win, Great Teams Cover. The short version is it happened during Wild Card weekend. There was one obvious ‘safe’ pick, and the other three games were toss-ups.

Knowing most of the people left would take the safe pick I stayed away.

Turns out everyone else lost when the ‘safe’ pick was upset leaving me with the pot.

The lesson learned was to win the big money you need to take a chance and go against the public.


Daniel Sroczyński – SallyBoom.com

So let be honest; betting tips could be hard to deal in some long period of time. So sharing the biggest win, it’s always a great story and comfortable feeling if you won it and some people who follow your tips also got it 😉

In my last couple of years I got many and many great and biggest wins with horse racing.

But the one I remember the most is the historic horse “Arabian Queen” with Silvester De Sousa on the board. This was my tip.

It was posted around 1 hour before the race started but I catch up ODD 81.00 at bet365.

This was like normal bet from me, almost all betting experts, players and my followers on every website know how I play. I’m aggressive tipster but my statistic show, that maybe I’m aggressive, but I know what I’m doing.

I managed to get over 35% yield after few thousands of tips 😉

About Arabic Queen; this horse was completely overpriced for me, with great training stamina, the great distance she caught up my eye in this race.

After all, I was still waiting for a booked jockey, when I saw that on the board will be the champion jockey Silvestre De Sousa it was for me best bet of the day.

It was funny how many tipsters around the world was betting against them because no know knows how much potential this horse was.

It was still a shaky bet but for me playing odds highest than 20.00 is almost a normal thing.

There was many also winners with bets 41.00/51.00/31.00/21.00 etc. But This one I like the one I like the most because it shows that experience in one sport could be profitable for you if you just know what to do and of course how to do it.

Some short info about the race can be found here.


Carlos Evans – LottoDog.co.uk

My biggest win yet – patience and consistency finally pay off, BIG!

You can only imagine how I must feel when it’s an international break, and England plays Spain (Spanish father, English mother), but I guess that confliction is what ultimately led to the development of my winning sports betting strategy, which resulted in my biggest win yet.

So I don’t bet on international matches; too many people manage to predict the results.

I simply bet “lose” on about 40-50% of the teams everyone expects to win, take hits for a long time and then finally win BIG when two or more of these sure fire “bankers” lose over the same weekend.


Michael- FoxyMonkey.com

I have indeed experience in betting and my specialisation lies in arbitrage and matched betting.

Speaking of big wins, you probably know I’m a slow and steady winner rather than a huge win once in a while.

For example, I have proven I can consistently earn £600-700 per month by sitting on the couch and occasionally taking advantage of offers. That’s about £7,200 per year, tax-free, risk-free.


Steve Merril – ProSportsInfo.com

The key to winning long-term is consistency.

This is particularly the case in regards to money management. I rate all my games as 3% of bankroll. Therefore; all my wins are equal.

While this maybe prevents having a huge win, it, more importantly, prevents any huge loss.

If a win feels big, then you are probably playing too much on that game and not staying with the proper parameters of your money management system.

The same in regards to a loss. No single game should ever affect your overall long-term ROI (return on investment).


The End

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