Dave, 54, and Ray Dunning, 55, both from Copnor each placed a £100 stake on Leicester to win the league back in December with odds of 28-1.
The pair received a payout of £2,900 – the £2,800 win plus their stake back – each from Betfred and are celebrating after Leicester were confirmed as champions on Monday.
The brothers, who own B&D roofing contractors on Copnor Road are delighted to have won the money, with both already making plans with their prize money.
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Dave, of Tokio Road said: ‘I’ve given £100 each to my four daughters and have booked to go to Cornwall this summer with my wife.’
The punters, both primarily Pompey fans, have been watching Leicester’s games together since placing their bet on December 7.
Dave said: ‘Because we put the money on together, we’ve been watching all their games with a beer every week – we’re Leicester fans for life now.’
He said: ‘We normally do a £20 bet each every week but we fancied Leicester to win it back in December and the odds were pretty good.’
Leicester, who were 5,000-1 to win the Premier League before a ball was kicked in August, sealed the championship on Monday after Spurs drew at Chelsea and the brothers watched on in anticipation.
Ray, of Langstone Road, said: ‘Nervous was an understatement, we were sat there biting our fingernails off.
‘But I’m over the moon that they have won it, I’ve never had this sort of money before.’
He said: ‘I get to take my two boys on holiday as well, we’re off to Disneyland Florida in August so they’re as happy as I am.’
The roofers have taken some time off work as well as they celebrate with their winnings. ‘We’ve both taken the week off and given ourselves a little break for now,’ said Ray. ‘I went into the bookies and went round the back where they counted out the money – I couldn’t believe it.’