Sidemen manager Billy Wingrove made history as the Premier League's first freestyle coach years before making it big with F2 Freestylers.
The 40-year-old online sensation will take charge of the Sidemen FC squad at the London Stadium on Saturday after leading them to an 8-7 win at the Valley over the YouTube All-Stars last year.
Wingrove, best known for being half of F2 alongside Jeremy Lynch, kicked off a career in the sport back in 2003 despite failing to impress during a trial at his boyhood club.
Brushing off that disappointment, he became the first professional freestyle footballer to sign for a Premier League club in the form of Tottenham while in his teens, helping youngsters and even performing during half-time breaks and at corporate events.
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He said at the time: "I started with a small football when I was much younger – if you do that, by the time you get to a bigger one it becomes a lot easier – and I've been practising all my life.
"Now all of a sudden it has become my job. When I was about 16 I entered a freestyle competition and got to the semi-finals out of about 30,000 contestants.
"An agent then approached me and asked if I would like to do it professionally and things have gone on from there."
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It was in 2011 that his career went to the next level with F2, who have since brought in 14 million subscribers and over three billion views.
He has also branched out into the Wingrove family YouTube channel which has over a million subscribers, filming videos with wife Katie and their three young children.
Putting his channels to one side this weekend, Wingrove will oversee the likes of KSI, Miniminter, Behzinga, Vikkstar123 and more as they look for a fourth win from five events.
Wingrove was the boss back in 2022 for the first match in four years, with Mark Goldbridge again his opposite number.
Other stars involved include Speed, Theo Baker, MrBeast, Chunkz and Yung Filly, with the game being streamed on the Sidemen YouTube Channel from the home of West Ham.
Wingrove and Lynch have managed to find success with F2 despite supporting north London rivals.
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He told Spurs on his return to the ground in 2021: "With me and Jez it's fun cause obviously he's a big Arsenal fans and I'm a huge Spurs fan.
"During the year we can have banter about it but when Spurs player Arsenal with literally don't talk.
"We tried once, one memory was in the old stadium the banter between us when from playful to now we're getting serious we need to cut this out!"
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