Throughout their tenure in the CPSL/CSL, Windsor won two Open Canada Cups, one American Indoor Soccer League (AISL) Championship, and maintained a status of regular playoff contender.

Around the 2008 CSL season, the club faced financial and player commitment problems which resulted in the league revoking the franchise.

The team is affiliated with the Toronto FC Academy, with the club's youth teams operating as Windsor TFC On December 23, 2003 the Canadian Professional Soccer League granted a franchise to Windsor under the joint ownership of former soccer player Jeff Hodgson, John Dowhan, and Gary Maccagnone.

On January 24, 2004 the Windsor Border Stars were revealed to the public, and former Blackburn Rovers player Pat Hilton was announced the club's first head coach.

Notable acquisitions were Alan Placek, Jeremy Harkins, Tati Errecalde, Tino Scicluna, Filip Rocca, Chris King, and Scott Patriquin.

[citation needed] In the regular season the team finished third in the Western Conference, and faced Oakville Blue Devils in the postseason.

[citation needed] For the 2006 season, the CPSL renamed itself the Canadian Soccer League (CSL), and the International and National divisions were created to replace the Western, and Eastern Conferences.

In preparation for the 2006 CSL season, Windsor acquired the services of former NPSL players Worteh Sampson, Dominic Scicluna, and Will Kletzien.

[5] The season marked an end to Windsor's run as Open Canada Cup champions as the Border Stars suffered a quarterfinal loss to Ottawa St. Anthony Italia.

[citation needed] In the regular season Windsor managed to secure the final playoff berth in the National Division.

In the first round of the postseason Windsor faced Oakville and avenged their previous quarterfinal loss with a 2–1 victory with goals from Sampson, and Kletzien.

[citation needed] In the next round the Border Stars faced division champions the Serbian White Eagles, but suffered a 6–1 defeat.

[6] In early 2011, the league announced that former Border Star defender, Filip Rocca, was awarded a franchise and would resurrect the club in Windsor.

[8][9] Windsor brought back veterans Byrd, Anthony Santilli, Gino Berardi, and signed Canadian international Stephen Ademolu.

[11] With home games being played at McHugh Park in Windsor, the club sought funding to turn the field into a stadium with proper seating and scoreboard to boost interest in the area.

They are consistently hosting development camps and clinics with different high level coaches from places like Toronto FC, or various universities where kids are able to train with the best and get identified based on their skill.