Updated: 5/12/09

Final
Date	Home Team	Away Team	Goals	Goal Scorers
01/12/09	Caledonia AIA	Joe Public FC
Semi-Final Round
Date	Home Team	Away Team	Goals	Goal Scorers
04/12/09	Defence Force	Caledonia AIA	0-1
				Kareem Joseph (82')
04/12/09	Ma Pau SC	Joe Public FC	0-1
				Hayden Tinto (13')
Quarter-Final Round
Date	Home Team	Away Team	Goals	Goal Scorers
20/11/09	Joe Public FC	Police FC	9-1	Hayden Tinto (14’, 81’, 83’), Seon Power (26’), Kerry Baptiste (44’, 56’, 76’, 80’), Jean-Luc Rocheford (63’)
				Hayden Jones (76’)
20/11/09	Ma Pau SC	W Connection FC	3-0	Trevin Caesar (60’), Shandell Samuel (79’, 89’)
20/11/09	Caledonia AIA	St. Ann's Rangers	5-0	Kendall Velox (15’, 56’, 65’), Stephan David (36’), Walter Moore (86’)
20/11/09	San Juan Jabloteh	Defence Force	1-2	Hector Sam (52')
				Jerwyn Balthazar (29’), Devon Jorsling (58’)
Preliminary Round
Date	Home Team	Away Team	Goals	Goal Scorers
17/11/09	United Petrotrin	Police FC	1-2	Simeon Augustus (19')
				Randy Harris (29'), Ricardo Peltier (66')
17/11/09	FC South End	St. Ann's Rangers	0-1
				Josimar Belgrave (10')

2008 Courts Pro Bowl - Neal & Massy Caledonia AIA
2007 Courts Pro Bowl - Vibe CT 105 W Connection
2006 Courts Pro Bowl - CL Financial San Juan Jabloteh
2005 Pro League Pro Bowl - CL Financial San Juan Jabloteh
2004 Pro League Pro Bowl - Vibe CT 105 W Connection
2003 Pro Bowl - CL Financial San Juan Jabloteh
2002 Independence Bowl - Vibe CT 105 W Connection