The 2008 Trinidad and Tobago League Cup was the ninth season of the First Citizens Cup, which is the league cup competition for Trinidad and Tobago teams competing in the TT Pro League. The slogan for the year's league cup was No Room for Losers and was sponsored by First Citizens Bank for the eighth consecutive year.W Connection entered as the defending champions after having defeated Caledonia AIA 2–0 in the 2007 final for their fourth consecutive league cup title.

Seeding for the competition was determined from the league standings following the eighteenth league match day. The bottom four teams were placed in the qualifying round to determine which teams advance to the quarterfinals. The teams ranked from first to sixth advanced directly to the quarterfinals.

The automatic quarterfinal qualifiers in order of league position were: San Juan Jabloteh, W Connection, Caledonia AIA, United Petrotrin, Joe Public, and St. Ann's Rangers.

The schedule for the 2008 First Citizens Cup, as announced by the TT Pro League:

All matches were played for 90 minutes duration, at the end of which if the match was still tied, penalty-kicks were used to determine the match winner.

The knockout cup began in the qualifying round with Tobago United and Defence Force recording upsets over higher-seeded Ma Pau and North East Stars respectively.

Fans saw a goal spree in the quarterfinals where 22 goals were scored in four matches on 12 September, which saw Jabloteh, Joe Public, Rangers, and W Connection advance to the semifinals.

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