| England in West Indies Test Series | 1929/30 | drawn | 1-1 (4) |
| England in West Indies Test Series | 1934/35 | West Indies | 2-1 (4) |
| England in West Indies Test Series | 1947/48 | West Indies | 2-0 (4) |
| India in West Indies Test Series | 1952/53 | West Indies | 1-0 (5) |
| England in West Indies Test Series | 1953/54 | drawn | 2-2 (5) |
| Australia in West Indies Test Series | 1955 | Australia | 3-0 (5) |
| Pakistan in West Indies Test Series | 1957/58 | West Indies | 3-1 (5) |
| England in West Indies Test Series | 1959/60 | England | 1-0 (5) |
| India in West Indies Test Series | 1961/62 | West Indies | 5-0 (5) |
| The Frank Worrell Trophy (Australia in West Indies) | 1964/65 | West Indies | 2-1 (5) |
| The Wisden Trophy (England in West Indies) | 1967/68 | England | 1-0 (5) |
| India in West Indies Test Series | 1970/71 | India | 1-0 (5) |
| New Zealand in West Indies Test Series | 1971/72 | drawn | 0-0 (5) |
| The Frank Worrell Trophy (Australia in West Indies) | 1972/73 | Australia | 2-0 (5) |
| The Wisden Trophy (England in West Indies) | 1973/74 | drawn | 1-1 (5) |
| India in West Indies Test Series | 1975/76 | West Indies | 2-1 (4) |
| Pakistan in West Indies Test Series | 1976/77 | West Indies | 2-1 (5) |
| The Frank Worrell Trophy (Australia in West Indies) | 1977/78 | West Indies | 3-1 (5) |
| The Wisden Trophy (England in West Indies) | 1980/81 | West Indies | 2-0 (4) |
| India in West Indies Test Series | 1982/83 | West Indies | 2-0 (5) |
| The Frank Worrell Trophy (Australia in West Indies) | 1983/84 | West Indies | 3-0 (5) |
| New Zealand in West Indies Test Series | 1984/85 | West Indies | 2-0 (4) |
| The Wisden Trophy (England in West Indies) | 1985/86 | West Indies | 5-0 (5) |
| Pakistan in West Indies Test Series | 1987/88 | drawn | 1-1 (3) |
| India in West Indies Test Series | 1988/89 | West Indies | 3-0 (4) |
| The Wisden Trophy (England in West Indies) | 1989/90 | West Indies | 2-1 (4) |
| The Frank Worrell Trophy (Australia in West Indies) | 1990/91 | West Indies | 2-1 (5) |
| South Africa in West Indies Test Match | 1991/92 | West Indies | 1-0 (1) |
| Pakistan in West Indies Test Series | 1992/93 | West Indies | 2-0 (3) |
| The Wisden Trophy (England in West Indies) | 1993/94 | West Indies | 3-1 (5) |
| The Frank Worrell Trophy (Australia in West Indies) | 1994/95 | Australia | 2-1 (4) |
| New Zealand in West Indies Test Series | 1995/96 | West Indies | 1-0 (2) |
| India in West Indies Test Series | 1996/97 | West Indies | 1-0 (5) |
| Sri Lanka in West Indies Test Series | 1997 | West Indies | 1-0 (2) |
| The Wisden Trophy (England in West Indies) | 1997/98 | West Indies | 3-1 (6) |
| The Frank Worrell Trophy (Australia in West Indies) | 1998/99 | drawn | 2-2 (4) |
| Zimbabwe in West Indies Test Series | 1999/00 | West Indies | 2-0 (2) |
| Pakistan in West Indies Test Series | 2000 | West Indies | 1-0 (3) |
| Sir Vivian Richards Trophy (South Africa in West Indies) | 2000/01 | South Africa | 2-1 (5) |
| India in West Indies Test Series | 2002 | West Indies | 2-1 (5) |
| New Zealand in West Indies Test Series | 2002 | New Zealand | 1-0 (2) |
| The Frank Worrell Trophy (Australia in West Indies) | 2003 | Australia | 3-1 (4) |
| Sri Lanka in West Indies Test Series | 2003 | West Indies | 1-0 (2) |
| The Wisden Trophy (England in West Indies) | 2003/04 | England | 3-0 (4) |
| Bangladesh in West Indies Test Series | 2004 | West Indies | 1-0 (2) |
| Sir Vivian Richards Trophy (South Africa in West Indies) | 2005 | South Africa | 2-0 (4) |
| Pakistan in West Indies Test Series | 2005 | drawn | 1-1 (2) |
| India in West Indies Test Series | 2006 | India | 1-0 (4) |
| Sri Lanka in West Indies Test Series | 2007/08 | drawn | 1-1 (2) |
| The Frank Worrell Trophy (Australia in West Indies) | 2008 | Australia | 2-0 (3) |
| The Wisden Trophy (England in West Indies) | 2008/09 | West Indies | 1-0 (5) |
| Bangladesh in West Indies Test Series | 2009 | Bangladesh | 2-0 (2) |
| Sir Vivian Richards Trophy (South Africa in West Indies) | 2010 | South Africa | 2-0 (3) |
| Pakistan in West Indies Test Series | 2011 | drawn | 1-1 (2) |
| India in West Indies Test Series | 2011 | India | 1-0 (3) |
| The Frank Worrell Trophy (Australia in West Indies) | 2011/12 | Australia | 2-0 (3) |
| New Zealand in West Indies Test Series | 2012 | West Indies | 2-0 (2) |
| Clive Lloyd Trophy (Zimbabwe in West Indies) | 2012/13 | West Indies | 2-0 (2) |
| New Zealand in West Indies Test Series | 2014 | New Zealand | 2-1 (3) |
| Bangladesh in West Indies Test Series | 2014 | West Indies | 2-0 (2) |
| The Wisden Trophy (England in West Indies) | 2015 | drawn | 1-1 (3) |
| The Frank Worrell Trophy (Australia in West Indies) | 2015 | Australia | 2-0 (2) |
| India in West Indies Test Series | 2016 | India | 2-0 (4) |
| Pakistan in West Indies Test Series | 2017 | Pakistan | 2-1 (3) |
| Sobers/Tissera Trophy (Sri Lanka in West Indies) | 2018 | drawn | 1-1 (3) |
| Bangladesh in West Indies Test Series | 2018 | West Indies | 2-0 (2) |
| The Wisden Trophy (England in West Indies) | 2018/19 | West Indies | 2-1 (3) |
| India in West Indies Test Series | 2019 | India | 2-0 (2) |
| Sri Lanka in West Indies Test Series | 2020/21 | drawn | 0-0 (2) |
| Sir Vivian Richards Trophy (South Africa in West Indies) | 2021 | South Africa | 2-0 (2) |
| Pakistan in West Indies Test Series | 2021 | drawn | 1-1 (2) |
| Botham-Richards Trophy (England in West Indies) | 2021/22 | West Indies | 1-0 (3) |
| Bangladesh in West Indies Test Series | 2022 | West Indies | 2-0 (2) |
| India in West Indies Test Series | 2023 | India | 1-0 (2) |