Prior to the first Sidemen Charity Match, five members of the group (all except KSI and Vikkstar123) participated in the first EE Wembley Cup on 8 August 2015 as part of Sidemen United, a team that was established for the match.

The Wembley Cup would be held annually for three more years without Sidemen United (which effectively dissolved after their only match), although Sidemen members Wroetoshaw, TBJZL and KSI would participate in the 2017 Wembley Cup as part of Tekkers Town, who lost against Hashtag United 6–1.

[citation needed] The first Sidemen Charity Match was held at St Mary's Stadium, Southampton, on 3 June 2016, raising over £110,000 for the Saints Foundation.

[5] After a four-year hiatus, the fourth match in 2022 raised over £1,000,000 for CALM, Teenage Cancer Trust, Rays of Sunshine and M7 Education.

[12] The match raised over £2.4 million for CALM, Teenage Cancer Trust, Rays of Sunshine and M7Education.