Beginning in 1999, GMSA established the first of its league-wide Cup Competitions, with the creation of the GMSA Challenge Cup.

• Challenge Cup:  Originally, this league-wide open-draw single-elimination tournament was held at the end of the Fall season.  Beginning in 2001, it was limited to teams from the men's top two divisions who meet the qualification criteria. Currently, it includes 16 qualifying teams from the Premier League and Championship League men's teams.  Also in 2001, the Challenge Cup trophy was renamed in honor of Tommy Smith, a long-time GMSA player who passed away in 2000 following a sudden illness.
• Victory Cup:  This competition was created in 2001 as a separate open-draw, single-elimination tournament, also held at the end of the Fall season.  Originally including the bottom two divisions, it was expanded to include all qualifying teams from the Second, Third and Fourth Divisions, following the league expansion in 2007.  It now includes the 16 teams that qualify from the men's Conference League.
• Coed Cup: Created in 2000, this league-wide open-draw single elimination tournament is held at the end of the Fall season for all coed teams in all divisions that meet qualification criteria.