Previous winners

• 2001 : Sporting Club
• 2002 : Victory Boys
• 2003 : unknown
• 2004 : Juventus
• 2005 : C&D
• 2005/06 : C&D
• 2006/07 : D&P Connection FC (Philipsburg)

Teams (2006-07)

• D&P Connection FC
• Haitian United
• Jah Rebels
• Liberation Stars
  Liberation Stars
  The Liberation Stars are a Sint Maarten football club based in Philipsburg who competed in the Sint Maarten League while it was still in existence. The club has been reported to have been playing in Sint Maarten's top division since 2002, although the most recent records are from 2007....
  
  
• Lucian United
• Organized Youth
• United Warlords
• Victory Boys