Maitland-Niles started the 2020 FA Community Shield on 29 August, taking and scoring the second penalty in a penalty shoot-out win against Liverpool after the match ended 1–1. In the FA Community Shield, Maitland-Niles was awarded the man of the match. Maitland-Niles has struggled to secure a spot in Mikel Arteta's first team, with interest coming from West Brom and Southampton to sign on loan.