| 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 |
| 1959-09-11 | Lennox Boyd meets West Indies soccer team | | Jamaica Gleaner |
| 1959-09-12 | Athenian League v. Caribbean XI Line-up | | Wealdstone Football Club |
| 1959-09-12 | Athenian League v. Caribbean XI | | Wealdstone Football Club |
| 1959-09-12 | Athenian League v. Caribbean XI | | Wealdstone Football Club |
| 1959-09-12 | WI soccer players hurt in UK crash | | Jamaica Gleaner |
| 1959-09-13 | Carib Soccer Side Lose 7-2 | | Jamaica Gleaner |
| 1959-09-15 | Calling Caribbean Highlight | | Jamaica Gleaner |
| 1959-09-17 | Carib side 3-0 victors | | Jamaica Gleaner |
| 1959-09-21 | Carib soccer team lose sixth match | | Jamaica Gleaner |
| 1959-09-21 | Highlights of the BBC's Carib cast this week | | Jamaica Gleaner |
| 1959-09-23 | King's Lynn F.C. vs. Caribbean XI lineup | | King's Lynn FC Official Programme |
| 1959-09-23 | King's Lynn FC v Caribbean XI | | 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 |
| 1959-10-03 | Petersborough United vs Caribbean | | Peterborough United |
| 1959-10-04 | Carib soccer team lose 4-1 | | Jamaica Gleaner |
| 1959-10-07 | Barking v. Caribbean XI | | Barking FC |
| 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 |
