| 1929-04-10 | Win For Sailors | | Jamaica Gleaner |
| 1932-09-14 | Venezuelan Footballers Beat Trinidad | | Jamaica Gleaner |
| 1933-10-30 | Trinidad And B.G. Play To A 1-Goal Draw In Inter-Colony Match | | Jamaica Gleaner |
| 1933-11-01 | Trinidad Defeat Barbados, 3—1 In Inter-Colony Soccer | | Jamaica Gleaner |
| 1936-01-15 | Trinidadians Win Their Last Match And Sail Away | | Jamaica Gleaner |
| 1936-11-18 | C. Botha Tench Playing With His Club In Trinidad | | Jamaica Gleaner |
| 1947-02-09 | Trinidad Beat Schools 3-0 | | Jamaica Gleaner |
| 1947-02-10 | Trinidad Beats Combined Schools | Linesman | Jamaica Gleaner |
| 1947-02-11 | Trinidad, Superior, Beat The 'Dragons' 4-2 | Effat | Jamaica Gleaner |
| 1947-02-13 | Goalless Draw In First Colony Match | Linesman | Jamaica Gleaner |
| 1947-02-16 | 15,000 See Jamaica Beat Trinidad, 2-1 | Linesman | Jamaica Gleaner |
| 1947-02-18 | Lucas Hold Visitors In Spiritless Draw | Linesman | Jamaica Gleaner |
| 1947-02-20 | Trinidad Bow 1-0 In Third Footer 'Test' | Effat | Jamaica Gleaner |
| 1947-11-02 | Trinidad Footballers Beat British Guiana | | Jamaica Gleaner |
| 1947-11-05 | B. G. Beats Trinidad In First Intercolonial Match | | Jamaica Gleaner |
| 1947-11-09 | Trinidad Repeats: Jamaica Beaten 6-0 On Dry Ground | | Jamaica Gleaner |
| 1949-04-23 | Trinidad Footballers Expect To Have Little Trouble Beating Jamaica | Joclyn McCalla | Jamaica Gleaner |
| 1949-04-30 | Haitian Tour Of Trinidad Footballers | Joclyn McCalla | Jamaica Gleaner |
| 1949-05-03 | Jamaica Beats Trinidad 3-1 In First Test | | Jamaica Gleaner |
| 1949-05-05 | Jamaica Wins Football Series | G. St. C. Scotter | Jamaica Gleaner |
| 1952-02-19 | Carib Stars Impress In First Soccer Outing | | Jamaica Gleaner |
| 1953-08-11 | Jamaica Beat Trinidad 3-2 | | Jamaica Gleaner |
| 1957-01-22 | Jamaica one up in football series | | Jamaica Gleaner |
| 1957-01-22 | Jamaica win two-nil | | Jamaica Gleaner |
| 1959-09-09 | Dorset Beat Carib Side 4-2 | | Jamaica Gleaner |
