The club has won the Bermudian league title 4 times, in 2005, 2007, 2009 and 2013.

[1] They won their most recent title in March 2013 when Somerset Eagles beat Cougars' final challengers North Village Rams to pull them out of the title race.

[2] In the 2009–10 season, Devonshire Cougars won their first FA Cup after defeating the Somerset Eagles.

On 4 July 2012 they lost Bermudian international Tumaini Steede in a bike accident,[3] with coach Dennis Brown citing the 2012/13 season would be dedicated to Steede.

[4] Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply.