The automatic quarterfinal qualifiers in order of league position are: Joe Public, Caledonia AIA, Ma Pau, San Juan Jabloteh, United Petrotrin, and W Connection.
The knockout cup began with the 10th place playoff between the bottom two clubs in the 2009 season following Match Day 20, Tobago United and Police, on 1 September at Plymouth Recreation Grounds.
St. Ann's Rangers used three saves from Haitian Fortunato Valcourt from penalty kicks to defeat FC South End and advanced to face top-seed Joe Public.
The tournament was concluded on 2 October when Defence Force upset Joe Public 1–0 in Marvin Lee Stadium to claim their second First Citizens Cup title and end their six-year trophy drought.
On the other hand, Joe Public suffered their second consecutive defeat in the league cup final having lost to W Connection on penalty kicks in last year's edition.