All matches were played over two 45 minute halves, and in the process if the match were drawn at the end of regulation time, then two additional 15-minute halves were used, and if necessary, penalty kicks if still drawn after extra time.
First round The draw for the most prestigious knockout tournament held by the
Trinidad and Tobago Football Association was made on 24 November 2008 at its head office in
Port of Spain, Trinidad with ties played on 3 December 2008. The only
Pro League match-up featured
United Petrotrin against
North East Stars. All Pro League clubs advanced easily into the second round with a combined scoreline of 28–2.{{cite news |title = Pro-League powerhouses mince FA opponents
Second round The draw for the second round took place on 4 December 2008 and involved the 16 winning teams from the first round. These were from the following levels: • 7 from Level 1 (
TT Pro League) • 4 from Level 2 (
National Super League) • 5 from Level 3 (1 EFA Premier Division, 2 NFA Premier Division, 1 SFA Premier Division, 1 Tobago FA Premier Division) Matches in the second round were played on 7 December 2008.
1976 FC Phoenix and
WASA provided the Trophy's first two upsets over
Pro League clubs by putting out
Joe Public and
North East Stars, respectively.{{cite news |title = Joe Public ousted from FA Trophy
Quarterfinals The draw for the quarterfinals took place on 8 December 2008 and involved the 8 winning teams from the second round. These were from the following levels: • 5 from Level 1 (
TT Pro League) • 2 from Level 2 (
National Super League) • 1 from Level 3 (
Dathea Copious Suns of the Northern FA Premier Division) Matches in the quarterfinals were played on 10 December 2008.
WASA remained the only club from outside the
TT Pro League to advance to the semifinals after defeating
Dathea Copious Suns.{{cite news |title = WASA flow into FA Trophy 'semis' ---- ---- ---- ----
Semifinals The draw for the semifinals took place on 11 December 2008. It consisted of
Caledonia AIA,
Defence Force, and
W Connection from the
Pro League (1) and
WASA from the
National Super League (2). The semifinal matches took place at
Marvin Lee Stadium on 15 December 2008.
W Connection made quick work of
Super League side
WASA to end their run in the competition by putting up eight goals.{{cite news |title = Connection cruise into FA final ---- ----
Final The final was played at
Marvin Lee Stadium in
Macoya, Trinidad on 17 December 2008. The match was contested by
Caledonia AIA, who beat
Defence Force 4–2 in their semifinal, and
W Connection who beat
WASA 8–1. Caledonia AIA used a goal late from
Conrad Smith to level the match at two each in the 82nd minute.{{cite news |title = Caledonia claim historic FA crown ==References==