Paddy Miller, who is also a lifelong Leeds United supporter, initially came to the attention of Chicago Town pizza when he likened an image of the food offering at York City to one of their frozen pizzas.
Chicago Town replied and after a brief exchange and a cheeky request for some free pizza, Miller was set the challenge of getting 20,000 likes on a Tweet.
The 32-year-old set about enlisting the support of Leeds fans on Twitter and with a helping hand from the club's digital media manager Craig Wilson, who Retweeted his plea from the official Leeds United account to its 860,000 followers, the target was quickly surpassed.
At last count Miller's Tweet had over 28,000 likes and 1,300 Retweets.
Chicago Town were happy to oblige with a year's supply of pizza, but Miller has redirected the freebies to a city foodbank, via Leeds United Supporters Trust.
"It was just a bit of fun initially, but it then generated legs," said Miller.
"I didn't do anything really, just a few jokey tweets. They've agreed to donate the pizzas so I've created a chat with the Trust, Chicago Town and Boost Drinks who have come forward to make a donation as well. I'm leaving it with the Trust to ensure it's distributed to the right places.
"I'm happy for them all to go to the food banks. Being from Leeds and still living in the city I'd much rather it go to the community for something like this."
Miller, a commercial manager for McLaren Financial Services, first attended a game at Elland Road in 1996 and had a season ticket for eight years before his own football career got in the way.
He started playing at Yorkshire Amateurs and then had spells with Farsley Celtic, Tadcaster Albion, before joining Boro.
A spokesperson for the foodbank said: "We would like to thank Paddy and Chicago Town for the wonderful donation. The pizzas will be a great addition to the food parcels that we hand out across the city. Foodbank usage has increased massively recently and these will go a long way in supporting our clients”
Leeds United Supporters’ Trust say the club will reward Miller's generosity with a special gift for his efforts.
“It was a really selfless thing for Paddy to do, donating over 1000 pizzas he had won as a bet and by having a bit of fun," said a spokesperson.
"The difference this donation makes to Leeds families is massive and will be a treat for many who are struggling with the rising cost of living. The club have come forward and rewarded Paddy with a signed shirt and two tickets to a future game as a gesture for his kindness - as well as a free lifetime Supporters’ Trust membership. Leeds fans never cease to amaze us - well done Paddy.”