| West Indies in England Test Series, 1928 | 1928 | England | 3-0 (3) |
| England in West Indies Test Series, 1929/30 | 1929/30 | drawn | 1-1 (4) |
| West Indies in Australia Test Series, 1930/31 | 1930/31 | Australia | 4-1 (5) |
| West Indies in England Test Series, 1933 | 1933 | England | 2-0 (3) |
| England in West Indies Test Series, 1934/35 | 1934/35 | West Indies | 2-1 (4) |
| West Indies in England Test Series, 1939 | 1939 | England | 1-0 (3) |
| England in West Indies Test Series, 1947/48 | 1947/48 | West Indies | 2-0 (4) |
| West Indies in India Test Series, 1948/49 | 1948/49 | West Indies | 1-0 (5) |
| West Indies in England Test Series, 1950 | 1950 | West Indies | 3-1 (4) |
| West Indies in Australia Test Series, 1951/52 | 1951/52 | Australia | 4-1 (5) |
| West Indies in New Zealand Test Series, 1951/52 | 1951/52 | West Indies | 1-0 (2) |
| India in West Indies Test Series, 1952/53 | 1952/53 | West Indies | 1-0 (5) |
| England in West Indies Test Series, 1953/54 | 1953/54 | drawn | 2-2 (5) |
| Australia in West Indies Test Series, 1955 | 1955 | Australia | 3-0 (5) |
| West Indies in New Zealand Test Series, 1955/56 | 1955/56 | West Indies | 3-1 (4) |
| West Indies in England Test Series, 1957 | 1957 | England | 3-0 (5) |
| Pakistan in West Indies Test Series, 1957/58 | 1957/58 | West Indies | 3-1 (5) |
| West Indies in India Test Series, 1958/59 | 1958/59 | West Indies | 3-0 (5) |
| West Indies in Pakistan Test Series, 1958/59 | 1958/59 | Pakistan | 2-1 (3) |
| England in West Indies Test Series, 1959/60 | 1959/60 | England | 1-0 (5) |
| The Frank Worrell Trophy (West Indies in Australia), 1960/61 | 1960/61 | Australia | 2-1 (5) |
| India in West Indies Test Series, 1961/62 | 1961/62 | West Indies | 5-0 (5) |
| The Wisden Trophy (West Indies in England), 1963 | 1963 | West Indies | 3-1 (5) |
| The Frank Worrell Trophy (Australia in West Indies), 1964/65 | 1964/65 | West Indies | 2-1 (5) |
| The Wisden Trophy (West Indies in England), 1966 | 1966 | West Indies | 3-1 (5) |
| West Indies in India Test Series, 1966/67 | 1966/67 | West Indies | 2-0 (3) |
| The Wisden Trophy (England in West Indies), 1967/68 | 1967/68 | England | 1-0 (5) |
| The Frank Worrell Trophy (West Indies in Australia), 1968/69 | 1968/69 | Australia | 3-1 (5) |
| West Indies in New Zealand Test Series, 1968/69 | 1968/69 | drawn | 1-1 (3) |
| The Wisden Trophy (West Indies in England), 1969 | 1969 | England | 2-0 (3) |
| India in West Indies Test Series, 1970/71 | 1970/71 | India | 1-0 (5) |
| New Zealand in West Indies Test Series, 1971/72 | 1971/72 | drawn | 0-0 (5) |
| The Frank Worrell Trophy (Australia in West Indies), 1972/73 | 1972/73 | Australia | 2-0 (5) |
| The Wisden Trophy (West Indies in England), 1973 | 1973 | West Indies | 2-0 (3) |
| The Wisden Trophy (England in West Indies), 1973/74 | 1973/74 | drawn | 1-1 (5) |
| West Indies in India Test Series, 1974/75 | 1974/75 | West Indies | 3-2 (5) |
| West Indies in Pakistan Test Series, 1974/75 | 1974/75 | drawn | 0-0 (2) |
| The Frank Worrell Trophy (West Indies in Australia), 1975/76 | 1975/76 | Australia | 5-1 (6) |
| India in West Indies Test Series, 1975/76 | 1975/76 | West Indies | 2-1 (4) |
| The Wisden Trophy (West Indies in England), 1976 | 1976 | West Indies | 3-0 (5) |
| Pakistan in West Indies Test Series, 1976/77 | 1976/77 | West Indies | 2-1 (5) |
| The Frank Worrell Trophy (Australia in West Indies), 1977/78 | 1977/78 | West Indies | 3-1 (5) |
| West Indies in India Test Series, 1978/79 | 1978/79 | India | 1-0 (6) |
| The Frank Worrell Trophy (West Indies in Australia), 1979/80 | 1979/80 | West Indies | 2-0 (3) |
| West Indies in New Zealand Test Series, 1979/80 | 1979/80 | New Zealand | 1-0 (3) |
| The Wisden Trophy (West Indies in England), 1980 | 1980 | West Indies | 1-0 (5) |
| West Indies in Pakistan Test Series, 1980/81 | 1980/81 | West Indies | 1-0 (4) |
| The Wisden Trophy (England in West Indies), 1980/81 | 1980/81 | West Indies | 2-0 (4) |
| The Frank Worrell Trophy (West Indies in Australia), 1981/82 | 1981/82 | drawn | 1-1 (3) |
| India in West Indies Test Series, 1982/83 | 1982/83 | West Indies | 2-0 (5) |
| West Indies in India Test Series, 1983/84 | 1983/84 | West Indies | 3-0 (6) |
| The Frank Worrell Trophy (Australia in West Indies), 1983/84 | 1983/84 | West Indies | 3-0 (5) |
| The Wisden Trophy (West Indies in England), 1984 | 1984 | West Indies | 5-0 (5) |
| The Frank Worrell Trophy (West Indies in Australia), 1984/85 | 1984/85 | West Indies | 3-1 (5) |
| New Zealand in West Indies Test Series, 1984/85 | 1984/85 | West Indies | 2-0 (4) |
| The Wisden Trophy (England in West Indies), 1985/86 | 1985/86 | West Indies | 5-0 (5) |
| West Indies in Pakistan Test Series, 1986/87 | 1986/87 | drawn | 1-1 (3) |
| West Indies in New Zealand Test Series, 1986/87 | 1986/87 | drawn | 1-1 (3) |
| West Indies in India Test Series, 1987/88 | 1987/88 | drawn | 1-1 (4) |
| Pakistan in West Indies Test Series, 1987/88 | 1987/88 | drawn | 1-1 (3) |
| The Wisden Trophy (West Indies in England), 1988 | 1988 | West Indies | 4-0 (5) |
| The Frank Worrell Trophy (West Indies in Australia), 1988/89 | 1988/89 | West Indies | 3-1 (5) |
| India in West Indies Test Series, 1988/89 | 1988/89 | West Indies | 3-0 (4) |
| The Wisden Trophy (England in West Indies), 1989/90 | 1989/90 | West Indies | 2-1 (4) |
| West Indies in Pakistan Test Series, 1990/91 | 1990/91 | drawn | 1-1 (3) |
| The Frank Worrell Trophy (Australia in West Indies), 1990/91 | 1990/91 | West Indies | 2-1 (5) |
| The Wisden Trophy (West Indies in England), 1991 | 1991 | drawn | 2-2 (5) |
| South Africa in West Indies Test Match, 1991/92 | 1991/92 | West Indies | 1-0 (1) |
| The Frank Worrell Trophy (West Indies in Australia), 1992/93 | 1992/93 | West Indies | 2-1 (5) |
| Pakistan in West Indies Test Series, 1992/93 | 1992/93 | West Indies | 2-0 (3) |
| West Indies in Sri Lanka Test Match, 1993/94 | 1993/94 | drawn | 0-0 (1) |
| The Wisden Trophy (England in West Indies), 1993/94 | 1993/94 | West Indies | 3-1 (5) |
| West Indies in India Test Series, 1994/95 | 1994/95 | drawn | 1-1 (3) |
| West Indies in New Zealand Test Series, 1994/95 | 1994/95 | West Indies | 1-0 (2) |
| The Frank Worrell Trophy (Australia in West Indies), 1994/95 | 1994/95 | Australia | 2-1 (4) |
| The Wisden Trophy (West Indies in England), 1995 | 1995 | drawn | 2-2 (6) |
| New Zealand in West Indies Test Series, 1995/96 | 1995/96 | West Indies | 1-0 (2) |
| The Frank Worrell Trophy (West Indies in Australia), 1996/97 | 1996/97 | Australia | 3-2 (5) |
| India in West Indies Test Series, 1996/97 | 1996/97 | West Indies | 1-0 (5) |
| Sri Lanka in West Indies Test Series, 1997 | 1997 | West Indies | 1-0 (2) |
| West Indies in Pakistan Test Series, 1997/98 | 1997/98 | Pakistan | 3-0 (3) |
| The Wisden Trophy (England in West Indies), 1997/98 | 1997/98 | West Indies | 3-1 (6) |
| West Indies in South Africa Test Series, 1998/99 | 1998/99 | South Africa | 5-0 (5) |
| The Frank Worrell Trophy (Australia in West Indies), 1998/99 | 1998/99 | drawn | 2-2 (4) |
| West Indies in New Zealand Test Series, 1999/00 | 1999/00 | New Zealand | 2-0 (2) |
| Zimbabwe in West Indies Test Series, 1999/00 | 1999/00 | West Indies | 2-0 (2) |
| Pakistan in West Indies Test Series, 2000 | 2000 | West Indies | 1-0 (3) |
| The Wisden Trophy (West Indies in England), 2000 | 2000 | England | 3-1 (5) |
| The Frank Worrell Trophy (West Indies in Australia), 2000/01 | 2000/01 | Australia | 5-0 (5) |
| Sir Vivian Richards Trophy (South Africa in West Indies), 2000/01 | 2000/01 | South Africa | 2-1 (5) |
| Clive Lloyd Trophy (West Indies in Zimbabwe), 2001 | 2001 | West Indies | 1-0 (2) |
| West Indies in Sri Lanka Test Series, 2001/02 | 2001/02 | Sri Lanka | 3-0 (3) |
| Pakistan v West Indies Test Series (in United Arab Emirates), 2001/02 | 2001/02 | Pakistan | 2-0 (2) |
| India in West Indies Test Series, 2002 | 2002 | West Indies | 2-1 (5) |
| New Zealand in West Indies Test Series, 2002 | 2002 | New Zealand | 1-0 (2) |
| West Indies in India Test Series, 2002/03 | 2002/03 | India | 2-0 (3) |
| West Indies in Bangladesh Test Series, 2002/03 | 2002/03 | West Indies | 2-0 (2) |
| The Frank Worrell Trophy (Australia in West Indies), 2003 | 2003 | Australia | 3-1 (4) |
| Sri Lanka in West Indies Test Series, 2003 | 2003 | West Indies | 1-0 (2) |
| Clive Lloyd Trophy (West Indies in Zimbabwe), 2003/04 | 2003/04 | West Indies | 1-0 (2) |
| Sir Vivian Richards Trophy (West Indies in South Africa), 2003/04 | 2003/04 | South Africa | 3-0 (4) |
| The Wisden Trophy (England in West Indies), 2003/04 | 2003/04 | England | 3-0 (4) |
| Bangladesh in West Indies Test Series, 2004 | 2004 | West Indies | 1-0 (2) |
| The Wisden Trophy (West Indies in England), 2004 | 2004 | England | 4-0 (4) |
| Sir Vivian Richards Trophy (South Africa in West Indies), 2005 | 2005 | South Africa | 2-0 (4) |
| Pakistan in West Indies Test Series, 2005 | 2005 | drawn | 1-1 (2) |
| West Indies in Sri Lanka Test Series, 2005 | 2005 | Sri Lanka | 2-0 (2) |
| The Frank Worrell Trophy (West Indies in Australia), 2005/06 | 2005/06 | Australia | 3-0 (3) |
| West Indies in New Zealand Test Series, 2005/06 | 2005/06 | New Zealand | 2-0 (3) |
| India in West Indies Test Series, 2006 | 2006 | India | 1-0 (4) |
| West Indies in Pakistan Test Series, 2006/07 | 2006/07 | Pakistan | 2-0 (3) |
| The Wisden Trophy (West Indies in England), 2007 | 2007 | England | 3-0 (4) |
| Sir Vivian Richards Trophy (West Indies in South Africa), 2007/08 | 2007/08 | South Africa | 2-1 (3) |
| Sri Lanka in West Indies Test Series, 2007/08 | 2007/08 | drawn | 1-1 (2) |
| The Frank Worrell Trophy (Australia in West Indies), 2008 | 2008 | Australia | 2-0 (3) |
| West Indies in New Zealand Test Series, 2008/09 | 2008/09 | drawn | 0-0 (2) |
| The Wisden Trophy (England in West Indies), 2008/09 | 2008/09 | West Indies | 1-0 (5) |
| The Wisden Trophy (West Indies in England), 2009 | 2009 | England | 2-0 (2) |
| Bangladesh in West Indies Test Series, 2009 | 2009 | Bangladesh | 2-0 (2) |
| The Frank Worrell Trophy (West Indies in Australia), 2009/10 | 2009/10 | Australia | 2-0 (3) |
| Sir Vivian Richards Trophy (South Africa in West Indies), 2010 | 2010 | South Africa | 2-0 (3) |
| West Indies in Sri Lanka Test Series, 2010/11 | 2010/11 | drawn | 0-0 (3) |
| Pakistan in West Indies Test Series, 2011 | 2011 | drawn | 1-1 (2) |
| India in West Indies Test Series, 2011 | 2011 | India | 1-0 (3) |
| West Indies in Bangladesh Test Series, 2011/12 | 2011/12 | West Indies | 1-0 (2) |
| West Indies in India Test Series, 2011/12 | 2011/12 | India | 2-0 (3) |
| The Frank Worrell Trophy (Australia in West Indies), 2011/12 | 2011/12 | Australia | 2-0 (3) |
| The Wisden Trophy (West Indies in England), 2012 | 2012 | England | 2-0 (3) |
| New Zealand in West Indies Test Series, 2012 | 2012 | West Indies | 2-0 (2) |
| West Indies in Bangladesh Test Series, 2012/13 | 2012/13 | West Indies | 2-0 (2) |
| Clive Lloyd Trophy (Zimbabwe in West Indies), 2012/13 | 2012/13 | West Indies | 2-0 (2) |
| West Indies in India Test Series, 2013/14 | 2013/14 | India | 2-0 (2) |
| West Indies in New Zealand Test Series, 2013/14 | 2013/14 | New Zealand | 2-0 (3) |
| New Zealand in West Indies Test Series, 2014 | 2014 | New Zealand | 2-1 (3) |
| Bangladesh in West Indies Test Series, 2014 | 2014 | West Indies | 2-0 (2) |
| Sir Vivian Richards Trophy (West Indies in South Africa), 2014/15 | 2014/15 | South Africa | 2-0 (3) |
| The Wisden Trophy (England in West Indies), 2015 | 2015 | drawn | 1-1 (3) |
| The Frank Worrell Trophy (Australia in West Indies), 2015 | 2015 | Australia | 2-0 (2) |
| Sobers/Tissera Trophy (West Indies in Sri Lanka), 2015/16 | 2015/16 | Sri Lanka | 2-0 (2) |
| The Frank Worrell Trophy (West Indies in Australia), 2015/16 | 2015/16 | Australia | 2-0 (3) |
| India in West Indies Test Series, 2016 | 2016 | India | 2-0 (4) |
| Pakistan v West Indies Test Series (in United Arab Emirates), 2016/17 | 2016/17 | Pakistan | 2-1 (3) |
| Pakistan in West Indies Test Series, 2017 | 2017 | Pakistan | 2-1 (3) |
| The Wisden Trophy (West Indies in England), 2017 | 2017 | England | 2-1 (3) |
| West Indies in Zimbabwe Test Series, 2017/18 | 2017/18 | West Indies | 1-0 (2) |
| West Indies in New Zealand Test Series, 2017/18 | 2017/18 | New Zealand | 2-0 (2) |
| Sobers/Tissera Trophy (Sri Lanka in West Indies), 2018 | 2018 | drawn | 1-1 (3) |
| Bangladesh in West Indies Test Series, 2018 | 2018 | West Indies | 2-0 (2) |
| West Indies in India Test Series, 2018/19 | 2018/19 | India | 2-0 (2) |
| West Indies in Bangladesh Test Series, 2018/19 | 2018/19 | Bangladesh | 2-0 (2) |
| The Wisden Trophy (England in West Indies), 2018/19 | 2018/19 | West Indies | 2-1 (3) |
| India in West Indies Test Series, 2019 | 2019 | India | 2-0 (2) |
| Afghanistan v West Indies Test Match (in India), 2019/20 | 2019/20 | West Indies | 1-0 (1) |
| The Wisden Trophy (West Indies in England), 2020 | 2020 | England | 2-1 (3) |
| West Indies in New Zealand Test Series, 2020/21 | 2020/21 | New Zealand | 2-0 (2) |
| West Indies in Bangladesh Test Series, 2020/21 | 2020/21 | West Indies | 2-0 (2) |
| Sri Lanka in West Indies Test Series, 2020/21 | 2020/21 | drawn | 0-0 (2) |
| Sir Vivian Richards Trophy (South Africa in West Indies), 2021 | 2021 | South Africa | 2-0 (2) |
| Pakistan in West Indies Test Series, 2021 | 2021 | drawn | 1-1 (2) |
| West Indies in Sri Lanka Test Series, 2021/22 | 2021/22 | Sri Lanka | 2-0 (2) |
| Botham-Richards Trophy (England in West Indies), 2021/22 | 2021/22 | West Indies | 1-0 (3) |
| Bangladesh in West Indies Test Series, 2022 | 2022 | West Indies | 2-0 (2) |
| The Frank Worrell Trophy [West Indies in Australia], 2022/23 | 2022/23 | Australia | 2-0 (2) |
| West Indies in Zimbabwe Test Series, 2022/23 | 2022/23 | West Indies | 1-0 (2) |
| Sir Vivian Richards Trophy (West Indies in South Africa), 2022/23 | 2022/23 | South Africa | 2-0 (2) |
| India in West Indies Test Series, 2023 | 2023 | India | 1-0 (2) |
| The Frank Worrell Trophy (West Indies in Australia), 2023/24 | 2023/24 | drawn | 1-1 (2) |
| Botham-Richards Trophy (West Indies in England), 2024 | 2024 | England | 3-0 (3) |
| Sir Vivian Richards Trophy (South Africa in West Indies), 2024 | 2024 | South Africa | 1-0 (2) |
| Bangladesh in West Indies Test Series, 2024/25 | 2024/25 | drawn | 1-1 (2) |
| West Indies in Pakistan Test Series, 2024/25 | 2024/25 | drawn | 1-1 (2) |
| The Frank Worrell Trophy (Australia in West Indies), 2025 | 2025 | Australia | 3-0 (3) |