Results
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.
9th place playoff
| 3 September 2010 | FC South End | 2–1 | Police | Macoya, Trinidad |
| 19:00 (UTC-4) | Etienne  17'Modeste 80' |
Report | Williams 22' |
Stadium: Marvin Lee Stadium |
Qualifying round
| 18 September 2010 | North East Stars | 2–1 | FC South End | Macoya, Trinidad |
| 19:00 (UTC-4) | Morrison 80' (o.g.) Fraser 90+3' |
Report | Bacchus 48' |
Stadium: Marvin Lee Stadium |
Quarterfinals
| 1 October 2010 | Defence Force | 0–0 (2–1 p) | St. Ann's Rangers | Marabella, Trinidad |
| 18:00 (UTC-4) | Report | Stadium: Manny Ramjohn Stadium Referee: Neal Brizan | ||
| Penalties | ||||
Edwards  Thornhill |
Clarke |
|||
| 1 October 2010 | W Connection | 2–0 | Caledonia AIA | Marabella, Trinidad |
| 20:00 (UTC-4) | Viveros 47' Hector 85' |
Report | Stadium: Manny Ramjohn Stadium Referee: Neal Brizan |
| 2 October 2010 | Joe Public | 2–0 | North East Stars | Mucurapo, Trinidad |
| 18:00 (UTC-4) | Gregory 36' Baptiste 45' (pen.) |
Report | Stadium: Hasley Crawford Stadium |
| 2 October 2010 | Ma Pau | w/o | San Juan Jabloteh | Mucurapo, Trinidad |
| 20:00 (UTC-4) | Report | Stadium: Hasely Crawford Stadium Referee: Gordon Maloney |
Semifinals
| 15 October 2010 | Defence Force | 1–0 | Ma Pau | Macoya, Trinidad |
| 18:00 (UTC-4) | Edwards 34' |
Report | Stadium: Marvin Lee Stadium |
| 15 October 2010 | Joe Public | 3–1 | W Connection | Macoya, Trinidad |
| 20:00 (UTC-4) | Noel 30' Hoshide 81'Baptiste 90' |
Report | Arias 15' |
Stadium: Marvin Lee Stadium |
Final
| 23 October 2010 | Defence Force | 1–1 (0–3 p) | Joe Public | Macoya, Trinidad |
| 20:00 (UTC-4) | Jorsling 63' |
Report | Mitchell 79' |
Stadium: Marvin Lee Stadium Referee: Lee Davis |
| Penalties | ||||
Jorsling  Elcock Edwards |
Noel Toussaint Mitchell Hoshide |
|||