Results
All matches were played over two 45 minutes halves, and in the process if the match were drawn at the end of regulation time, penalty kicks determined the winner.
First round
On the competition's opening night, W Connection dumped Caledonia AIA out of the tournament with a 3–0 victory on penalty kicks after each team scored a goal in regulation.[1] There were no other surprises as Joe Public easily defeated Police, Ma Pau claimed a 2–1 victory over Joe Public (SL), and St. Ann's Rangers used a late Jahvon Morris goal to advance past fellow Pro League side FC South End. On the following day, Defence Force defeated T&TEC by a score 3–0, whereas San Juan Jabloteh mauled Defence Force (SL) 5–0 to advance to the quarterfinals.[2]
| 30 October 2009 | St. Ann's Rangers (1) | 3–2 | FC South End (1) | Malabar, Trinidad |
| 18:00 (UTC-4) | Musgrave  23', 55'Morris 88' |
Report | Etienne 34', 37' |
Stadium: Larry Gomes Stadium |
| 1 November 2009 | 1976 FC Phoenix (2) | 1–1 (4–3 p) | Harvard (2) | Malabar, Trinidad |
| 18:00 (UTC-4) | Noray 2' |
Report | Freitas 20' |
Stadium: Larry Gomes Stadium |
| 31 October 2009 | San Juan Jabloteh (1) | 5–0 | Defence Force (2) | Malabar, Trinidad |
| 18:00 (UTC-4) | Williams 16', 67' (pen.) Oliver 58', 72'Mulraine 79' |
Report | Stadium: Larry Gomes Stadium Referee: Neal Brizan |
| 30 October 2009 | United Petrotrin (1) | 2–1 | Economy Strikers (2) | Marabella, Trinidad |
| 18:00 (UTC-4) | Lima 32' Dwarika 85' |
Report | Hughes 90+2' |
Stadium: Manny Ramjohn Stadium |
| 31 October 2009 | Defence Force (1) | 3–0 | T&TEC (2) | Malabar, Trinidad |
| 20:00 (UTC-4) | Narcis 18' Balthazar 25'Carter 33' |
Report | Stadium: Larry Gomes Stadium |
| 30 October 2009 | Joe Public (1) | 4–1 | Police (1) | Macoya, Trinidad |
| 18:00 (UTC-4) | Noel 20' McKnight 24'Highley 82', 86' |
Report | Marshall 90' |
Stadium: Marvin Lee Stadium |
| 30 October 2009 | Joe Public (2) | 1–2 | Ma Pau (1) | Macoya, Trinidad |
| 20:00 (UTC-4) | Derrick 45' |
Report | Samuel 35', 60' |
Stadium: Marvin Lee Stadium |
| 30 October 2009 | W Connection (1) | 1–1 (3–0 p) | Caledonia AIA (1) | Marabella, Trinidad |
| 20:00 (UTC-4) | Oliveira 80' |
Report | Joseph 29' (o.g.) |
Stadium: Manny Ramjohn Stadium |
| Penalties | ||||
Seabra  Pereira Cupid |
Muhammed  Daniel Stewart |
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Quarterfinals
San Juan Jabloteh survived a scoreless match after regulation to defeat Petrotrin on penalties 3–2 and advanced to the semifinals. Likewise, St. Ann's Rangers needed eight penalty kicks to defeat the lone National Super League team left in the tournament, 1976 FC Phoenix.[3] Ma Pau and Joe Public continued their run to the semifinals with wins over Pro League sides W Connection and Defence Force respectively.
| 4 November 2009 | St. Ann's Rangers (1) | 2–2 (8–7 p) | 1976 FC Phoenix (2) | Couva, Trinidad |
| 17:00 (UTC-4) | Belgrave 45+1' (pen.) Thomas 61' |
Report | Grimshaw 21' Williams 88' |
Stadium: Ato Boldon Stadium Referee: Shane de Silva |
| Penalties | ||||
| Belgrave Narine Thomas Modeste Bristol Thomas Belgrave Williams |
Keith Williams Roberts Grimshaw Delpeche Mitchell Nedd Williams |
|||
| 3 November 2009 | San Juan Jabloteh (1) | 0–0 (3–2 p) | United Petrotrin (1) | Marabella, Trinidad |
| 18:00 (UTC-4) | Report | Stadium: Manny Ramjohn Stadium Referee: Mike Mohammed | ||
| Penalties | ||||
| Guerra Johnson Glen Williams |
Campbell Lima Pierre Hislop Glasgow |
|||
| 3 November 2009 | Defence Force (1) | 1–2 | Joe Public (1) | Macoya, Trinidad |
| 18:00 (UTC-4) | Balthazar 4' |
Smith 86', 90+3' |
Stadium: Marvin Lee Stadium |
| 3 November 2009 | Ma Pau (1) | 1–0 | W Connection (1) | Marabella, Trinidad |
| 20:00 (UTC-4) | Caesar 53' |
Stadium: Manny Ramjohn Stadium |
Semifinals
Jabloteh held off St. Ann's Rangers 4–3 following two late goals from Rangers to advance to the final on 13 November.[4] In the other semifinal match, Joe Public edged Ma Pau on penalties to meet Jabloteh in the final.
| 6 November 2009 | St. Ann's Rangers (1) | 3–4 | San Juan Jabloteh (1) | Macoya, Trinidad |
| 18:00 (UTC-4) | Modeste 15' Musgrave 90+2'Belgrave 90+4' |
Report | Williams 1', 52' Oliver 8', 45+1' |
Stadium: Marvin Lee Stadium |
| 6 November 2009 | Joe Public (1) | 1–1 (3–2 p) | Ma Pau (1) | Macoya, Trinidad |
| 20:00 (UTC-4) | Noel 83' |
Report | Andrews 76' |
Stadium: Marvin Lee Stadium |
| Penalties | ||||
| Noel Mitchell Hoshide Smith Rochford |
Wolfe Gonzales Freitas Samuel Noray |
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Final
Joe Public claimed the title on 13 November with a 4–0 mauling of Jabloteh at Marvin Lee Stadium. Although Jabloteh lost in the final, teammates Marvin Oliver and Noel Williams walked away as the tournament's top goal scorers with four goals each.
| 13 November 2009 | San Juan Jabloteh (1) | 0–4 | Joe Public (1) | Macoya, Trinidad |
| 20:00 (UTC-4) | Mitchell 14' Baptiste 24', 29'Tinto 65' |
Stadium: Marvin Lee Stadium |