| 1959-09-07 | Dorset County vs. Caribean F.A. | | Dorset County FA |
| 1959-09-09 | Dorset Beat Carib Side 4-2 | | Jamaica Gleaner |
| 1959-09-10 | Isthmian League v. Caribbean XI | | Dulwich Hamlet FC |
| 1959-09-10 | Isthmian League v. Caribbean XI | | Dulwich Hamlet FC |
| 1959-09-11 | Gomez, Gray Excel, But WI Lose 3-1 | | Jamaica Gleaner |
| 1959-09-23 | King's Lynn F.C. vs. Caribbean XI lineup | | King's Lynn FC Official Programme |
| 1959-09-26 | Carib Soccer Side Lose Seventh Match | | Jamaica Gleaner |
| 1959-10-01 | Carib Team Under Pressure | | Jamaica Gleaner |
| 1959-10-01 | Carib soccer team win third game 3-1 | | Jamaica Gleaner |
| 1959-10-03 | Petersborough United vs Caribbean | | Peterborough United |
| 1959-10-07 | Barking v. Caribbean XI | | Barking FC |
| 1959-10-09 | WI Soccer Team Edge Barking 2-1 | | Jamaica Gleaner |
| 1959-10-10 | Great Britain v. Caribbean F.A. | | Ipswich Town FC |
| 1959-10-10 | Great Britain v. Caribbean F.A. | | Ipswich Town FC |
| 1959-10-12 | Britain defeat West Indies 7-2 | | Jamaica Gleaner |
| 1959-10-14 | Crystal Palace v Caribbean FA lineup | | Crystal Palace FC |
| 1959-10-14 | Crystal Palace v. Caribbean F.A. XI | George Smith | Crystal Palace FC |
| 1959-10-16 | Crystal Palace give Carib side lesson in basic soccer arts | | Jamaica Gleaner |
| 1959-10-19 | Faulty Shooting Balks Carib Bid To Beat Pegasus | | Jamaica Gleaner |
| 1959-11-04 | Tour Players Should Be Used As Coaches | | Jamaica Gleaner |
| 1959-12-15 | Time And Money For WI Soccer Tour Well Spent | | Jamaica Gleaner |
| 1960-06-04 | Trinidad name team to play Wanderers | | Jamaica Gleaner |
| 1960-06-08 | Trinidad hold Wanderers to draw | | Jamaica Gleaner |
| 1960-09-21 | Trinidad Hold Martinique | | Jamaica Gleaner |
| 1960-09-26 | Trinidad south soccer titlists | | Jamaica Gleaner |
