Beginning in 1999, GMSA established the first of its league-wide Cup Competitions, with the creation of the GMSA Challenge Cup.
| Tommy Smith Challenge Cup Champions (Upper Division Fall Tournament) Inaugurated 1999: |
Victory Cup Champions (Lower Division Fall Tournament) Inaugurated 2001: |
Coed Cup Champions
(Coed Inter-Divisional Tournament) Inaugurated 2000: |
|
| 2009 | |||
| 2008 | Memphis Tigers FC | Strikers FC | Showboats FC |
| 2007 | Darkside FC | Memphis Crew FC | Those Guys FC |
| 2006 | FC Celtic | Rowdies FC | Dragons |
| 2005 | Memphis United FC | DeSoto United | Dragons |
| 2004 | Memphis United FC | Memphis Fire | Red Rovers |
| 2003 | FC Celtic | FC Europe | Hearts FC |
| 2002 | Kickers FC | Ring Rockets | Underdogs |
| 2001 | Flyers | Cambodian FC | Corsairs |
| 2000 | Flyers | --- | Corsairs |
| 1999 | Flyers | --- | --- |