The charity football matches were events hosted by the Sidemen from 2016 to 2018. Following a minor match they participated in for charity in 2015 (not hosted by them and known as The Wembley Cup), the Sidemen launched Sidemen F.C. in 2016 with their first official charity match, followed by a second in 2017, and a third in 2018. Following a 4-year hiatus, the Sidemen announced a fourth charity match in 2022.
|1||03/06/2016||St. Mary's||Saints Foundation||SDMN||7-2|
|2||21/05/2017||The Valley||CA Community Trust / Childline||YTAS||0-2|
|3||02/06/2018||The Valley||CA Community Trust / YoungMinds||SDMN||7-1|
- Main article: The Wembley Cup
The first football match that the Sidemen participated in for charity was hosted by Spencer FC in the summer of 2015. Five out of the seven Sidemen took part and played for a team called Sidemen United. The Wembley Cup (for YouTube) has continued every year since then, but 2015 was the only year in which Sidemen United was a team. They lost 5–2.
Despite the match taking place in Wembley Stadium and being live-streamed on YouTube, there were no tickets made available for fans to watch the match live.
- Main article: 2016 Charity Football Match
The Sidemen launched their own annual charity match events in 2016. The first took place on 3 June 2016 at St. Mary's Stadium in Southampton (home stadium of Southamption F.C.). Sidemen F.C. beat YouTube Allstars 7–2.
All money generated from this match went to the Saints Foundation - the official charity of Southampton Football Club. Around 15,000 people attended the match (just less than half the capacity of the stadium), with around 600,000 watching it live on YouTube. At the time, it was the biggest YouTube sporting event ever.
- Main article: 2017 Charity Football Match
Following the major success of the 2016 match, a second match was announced the following year and took place on 21 May 2017. Unlike the previous year, this match took place in The Valley stadium in London, home of Charlton Athletic F.C.. Although this stadium has a smaller capacity than St. Mary's, the Sidemen wanted to fill all the seats in the venue as opposed to just two stands.
Money generated from this second match went to the Charlton Athletic Community Trust and Childline. Sidemen F.C. once again went up against YouTube Allstars but this time lost 2–0. Both teams had different players than the 2016 match, but all the Sidemen remained on Sidemen F.C..
- Main article: 2018 Charity Football Match
A third match took place on 2 June 2018, and was announced in March of the same year. For the second year in a row, it took place at The Valley stadium with a victory of 7-1 for Sidemen F.C.. The chosen charities for this match were the Charlton Athletic Community Trust and YoungMinds . This was intended to be the final of the charity match events.
The event was sponsored by Pizza Hut who held various competitions in order to promote the event.
- Main article: 2022 Charity Football Match
Despite the 2018 match being touted as the final game, the possibility of a fourth charity match was discussed over the following years until it was officially confirmed in 2022. The match will once again take place at The Valley stadium in London.
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