Oct. 18, 2004 TRI1 2004 21 Drillers 3 - 1 Tobago United 1
Oct. 3, 2004 TRI1 2004 20 Arima Fire 5 - 0 Drillers 1
Sept. 26, 2004 TRI1 2004 19 Drillers 2 - 2 Strikers 1
Aug. 22, 2004 TRI1 2004 18 Drillers 0 - 8 NE Stars 1
Aug. 8, 2004 TRI1 2004 16 Drillers 0 - 2 W Connection 1
July 4, 2004 TRI1 2004 14 Drillers 4 - 1 Tobago United 1
June 30, 2004 TRI1 2004 13 Arima Fire 2 - 1 Drillers 1
June 27, 2004 TRI1 2004 12 Drillers 0 - 7 Strikers 1
June 23, 2004 TRI1 2004 11 Drillers 0 - 2 NE Stars 1
June 16, 2004 TRI1 2004 9 Drillers 0 - 5 W Connection 1
June 2, 2004 TRI1 2004 8 Drillers 1 - 2 San Juan Jabloteh 1
May 16, 2004 TRI1 2004 7 Drillers 3 - 0 Tobago United 1
May 12, 2004 TRI1 2004 6 Arima Fire 1 - 0 Drillers 1
May 9, 2004 TRI1 2004 5 Drillers 0 - 2 Strikers 1
May 5, 2004 TRI1 2004 4 Drillers 1 - 2 NE Stars 1