| 1989-11-19 |  Trinidad and Tobagov United StatesCONCACAF Championship | 0–1 | CONCACAF Championship |
| 1989-10-25 | Trinidad and Tobagov FinlandFriendly | 2–0 | Friendly |
| 1989-10-22 | Trinidad and TobagovFinlandFriendly | 0–1 | Friendly |
| 1989-09-03 | Trinidad and Tobagov GuatemalaCONCACAF Championship | 2–1 | CONCACAF Championship |
| 1989-09-01 | Trinidad and Tobagov PanamaFriendly | 2–0 | Friendly |
| 1989-08-20 | GuatemalavTrinidad and TobagoCONCACAF Championship | 0–1 | CONCACAF Championship |
| 1989-08-13 |  El SalvadorvTrinidad and TobagoCONCACAF Championship | 0–0 | CONCACAF Championship |
| 1989-07-30 | Trinidad and TobagovEl SalvadorCONCACAF Championship | 2–0 | CONCACAF Championship |
| 1989-07-09 |  GrenadavTrinidad and TobagoCFU Caribbean Cup | 1–2 | CFU Caribbean Cup |
| 1989-07-07 |  GuadeloupevTrinidad and TobagoCFU Caribbean Cup | 2–0 | CFU Caribbean Cup |
| 1989-07-05 |  BarbadosvTrinidad and TobagoCFU Caribbean Cup | 0–3 | CFU Caribbean Cup |
| 1989-06-16 | Trinidad and Tobagov PeruFriendly | 2–1 | Friendly |
| 1989-06-11 |  Costa RicavTrinidad and TobagoCONCACAF Championship | 1–0 | CONCACAF Championship |
| 1989-06-06 | GrenadavTrinidad and TobagoCFU Caribbean Cup qualification | 1–0 | CFU Caribbean Cup qualification |
| 1989-05-28 | Trinidad and TobagovCosta RicaCONCACAF Championship | 1–1 | CONCACAF Championship |
| 1989-05-21 |  Saint Kitts and NevisvTrinidad and TobagoCFU Caribbean Cup qualification | 0–2 | CFU Caribbean Cup qualification |
| 1989-05-13 | United StatesvTrinidad and TobagoCONCACAF Championship | 1–1 | CONCACAF Championship |
| 1989-05-10 |  French GuianavTrinidad and TobagoCFU Caribbean Cup qualification | 1–3 | CFU Caribbean Cup qualification |
| 1989-04-23 | Trinidad and Tobagov ArubaCFU Caribbean Cup qualification | 11–0 | CFU Caribbean Cup qualification |
| 1989-04-18 | Trinidad and Tobagov BermudaFriendly | 0–1 | Friendly |
| 1989-04-16 | Trinidad and TobagovBermudaFriendly | 1–1 | Friendly |
| 1989-04-01 |  Curaçaoplayed as Netherlands AntillesvTrinidad and TobagoFriendly | 1–1 | Friendly |
| 1989-03-31 | ArubavTrinidad and TobagoFriendly | 0–7 | Friendly |
| 1989-03-22 | Trinidad and Tobagov ParaguayFriendly | 1–1 | Friendly |
| 1989-03-19 | Trinidad and TobagovParaguayFriendly | 2–2 | Friendly |