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Martin Plunkett from Grimsby backed Henderson to play for his country when he was 14 years of age and in the Carlisle United youth academy.
Getting odds of 500/1 from William Hill, Martin whacked £25 on and all these years later his bet came in as Henderson earned his first Three Lions cap against Republic of Ireland last Thursday.
Henderson's mum and grandmother also collected £2,500 after the odds had come right down to 50/1 following his move to Manchester United.
Martin told The Mirror: "I haven't spoken to Dean about the bet but he did text after the game last Thursday to tell his mother, 'Have we all got the money?'
"Obviously we haven't been paid out yet. We say we're waiting for it. He's chuffed to bits.
"We told him we got confirmation from William Hill that the bet was alright so yeah, he was chuffed for us. He's a good lad. He deserves it.
"Anyone you ever spoke to who knew about him would tell you he'll go to the top.
"So obviously you have a little bet don't you? To be fair, it was only William Hill that would take the bet."
23-year-old Henderson signed a new and improved long-term contract with United following two impressive seasons on loan at Sheffield United.
He is now competing with Nick Pope and Jordan Pickford the England No.1 spot.
Henderson is the latest player involved in a story whereby a family has made serious money from a bet predicting their success.
For England, Chris Kirkland's father Eddie made £10,000 from a £100 bet at 100/1 after his son made his bow on the international stage, while Lewis Cook playing for the senior side in 2018 landed his grandfather £17,000 on a £500 wager he had placed four years earlier.
Elsewhere, Ryan Tunnicliffe's dad won £10,000 from a bet he placed when his son was nine after he made a first-team appearance for Man United.
However, the absolute best of the bunch involves Harry Wilson and his grandfather Peter Edwards.
Incredibly, he put a £50 bet on when the Liverpool man was just 18 months old and the gigantic odds of 2,500/1 saw him win a massive £125,000 after Wilson made his Wales debut as a 16-year-old back in 2013.
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