| Caledonia AIA | Morvant/Laventille | Larry Gomes Stadium | 10,000 | sortname|Jamaal|Shabazz
Season statisticsScoringFirst goal of the season: Nigel Codrington for Caledonia AIA against San Juan Jabloteh,.Last goal of the season: Conrad Smith for Caledonia AIA against San Juan Jabloteh,.First own goal of the season: Michael Edwards for Joe Public,.First penalty kick of the season: Kareem Joseph for Caledonia AIA against Tobago United.First hat-trick of the season: Kendall Jagdeosingh against Tobago United, 56', 59', 87'.Most goals scored by one player in a match: 3 goals
- * Kendall Jagdeosingh against Tobago United, 56', 59', 87'.
- * Errol McFarlane against Tobago United, 42', 81', 82'.
- * Peter Byers, 17', 35', 45'.
- * Errol McFarlane against Police, 34', 42', 75'.
- * Peter Prospar against Police, 51', 61', 68'.
- * Kayode Legall against Police, 62', 75', 90'.
- * Hayden Tinto against Tobago United, 56', 59', 70'.Widest winning margin: 7 goals
- * W Connection 7–0 Police Most goals in a match: 8 goals
- * Tobago United 6–2 Police
- * Tobago United 1–7 Caledonia AIA
- * North East Stars 7–1 Police Most goals in one half: 6 goals
- * Tobago United v San Juan Jabloteh 1–5 at half-time, 1–5 final.
- * Police v W Connection 1–0 at half-time, 4–3 final.
- * Tobago United v Police 2–0 at half-time, 6–2 final.
- * Tobago United v Joe Public 0–0 at half-time, 1–5 final.
- * North East Stars v Police 2–0 at half-time, 7–1 final.Most goals in one half by a single team: 5 goals
- * Tobago United v San Juan Jabloteh 1–5 at half-time, 1–5 final.
- * Tobago United v Joe Public 0–0 at half-time, 1–5 final.
- * W Connection v Police 2–0 at half-time, 7–0 final.
- * Tobago United v Caledonia AIA 1–2 at half-time, 1–7 final.
- * North East Stars v Police 2–0 at half-time, 7–1 final.
Top scorers| Rank | Player | Club | Goals | | 1 | 
Hat-tricks| Player | For | Against | Result | Date | Ref | sortname|Kendall|Jagdeosingh
AwardsAnnual awardsThe 2007 TT Pro League awards distribution took place on 5 April 2008, prior to the 2008 season's opening match at Hasely Crawford Stadium. The majority of the individual and team awards were shared by the league champion, San Juan Jabloteh, and the league's top trophy winner, W Connection. Marvin Oliver of Caledonia AIA was named the league's Player of the Year and Best Midfielder for the season. Each being Oliver's first recognition of his career. Peter Byers from Antigua and Barbuda received the Golden Boot and was named the Best Forward for leading the league with 15 goals. Stuart Charles-Fevrier became the first two-time winner of Manager of the Year after leading W Connection to two more cup trophies, a league third-place finish, and the Team of the Year award. Other individual awards were received by Jabloteh's Cleon John and W Connection's Elijah Joseph for Best Goalkeeper and Best Defender, respectively. The remaining team award was also won by the Savonetta Boys for the Most Disciplined Team of the Year. FIFA international referee, Neal Brizan, won the Referee of the Year, whereas Norris Ferguson won the Match Commissioner of the Year.
| Award | Winner | | Player of the Year | 
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