The GMSA Challenge Cup was established in 1999 as a league-wide, open draw, single-elimination tournament, as an alternative to our usual divisional tournaments. It was modified in 2001 to pit First Division teams against Second Division teams.

 At that time in 2001, the GMSA Victory Cup was then created for Third and Fourth Division teams, as a derivative of the original GMSA Challenge Cup. After the addition of the Premier Division in 2007, the format changed again.