Every week punters put on ridiculous accumulators with the hope that they strike gold.
The 22-year-old from Scunthorpe thought he'd try his luck by putting £1 on a seven game accumulator.
And he didn't sit on the fence.
Jack predicted some unlikely results, including Crystal Palace to beat Manchester United and Newcastle to beat Spurs.
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That meant that if all of his predictions came in, he would win £98,513,14.
Almost 70 minutes into the Saturday fixtures and everything was going well.
Chelsea had already beaten Norwich, while the four 3pm kickoff's he bet on were all coming in.
But Jack lost his nerve and cashed out for £200.
He would have thought that was a good result at the time but it turned out to be one of the worst decisions he had ever made.
Crystal Palace scored a late goals against United, meaning his first five predictions came in.
Man City then went on to beat Bournemouth comfortably the following day, before Newcastle produced a shock victory over Tottenham.
That meant he predicted all seven games correctly and would have won just under £100,000.
"During the Palace - Man United game, I'm a Man United fan and I just knew we were going to score," he said.
"The cash-out was about £200, but I knew United were going to score so I cashed out. Obviously Palace went and scored again.
"I thought it was alright because Spurs would do it anyway [against Newcastle United] so my bet is going to be let down anyway.
"To be fair, I should have let it run - it was only a quid, wasn't it? - but that's betting isn't it?
"Every week if you could ask for £200 from £1, you'd take it wouldn't you?
"Obviously this week though, there's about £90,000 out."
Oh Jack, you've had a shocker.News Now - Sport News