2004 Lawson Financial (19-4) - 1st Place.

2005 Platinum Financial (13-7) - 2nd Place. Winter Haven Senior Softball Club members who were teammates included Hugh Lessard & George Radlein and former member Al Pototnik. Former member Bill Dumas was the coach of the team.

2006 Masterpiece (9-8) - 3rd Place. WHSSC members who were teammates included Jose Agosto & Lloyd Hopper.

2007 Herman Johnson State Farm (11-10) - 2nd Place. WHSSC members who were teammates included Frank Acevedo & Bob Lundquest and former member Bill Dumas.

2008 Team (12-10) - Jerry Remington, a WHSSC member, was a teammate.

2009 Team (15-8) - Fred Dampier managed the team.

2010 Gene's Giants (9-9-1) - Fred Dampier managed the team. WHSSC members included sponsor Gene Morey and Frank Miller.