| 21 Dec 1959 | Marylebone Cricket Club in West Indies 1959/60 | | Windward Islands v Marylebone Cricket Club |
| 18 Mar 1961 | EW Swanton's XI in West Indies 1960/61 | | Windward Islands v EW Swanton's XI |
| 22 May 1965 | Australia in West Indies 1964/65 | | Windward Islands v Australians |
| 15 Mar 1967 | Shell Shield 1966/67 | | Windward Islands v Guyana |
| 25 Jan 1969 | Shell Shield 1968/69 | | Windward Islands v Jamaica |
| 20 Feb 1970 | Shell Shield 1969/70 | | Combined Leeward and Windward Islands v Trinidad and Tobago |
| 14 Apr 1973 | Australia in West Indies 1972/73 | | Windward Islands v Australians |
| 14 Mar 1975 | Shell Shield 1974/75 | | Combined Leeward and Windward Islands v Guyana |
| 07 Apr 1978 | Australia in West Indies and Bermuda 1977/78 | | Windward Islands v Australians |
| 06 Apr 1979 | Shell Shield 1978/79 | | Combined Leeward and Windward Islands v Jamaica |
| 07 Feb 1981 | Shell Shield 1980/81 | | Combined Leeward and Windward Islands v Guyana |
| 27 Mar 1982 | Shell Shield 1981/82 | | Windward Islands v Trinidad and Tobago |
| 18 Mar 1983 | India in West Indies 1982/83 | | Windward Islands v Indians |
| 17 Feb 1984 | Shell Shield 1983/84 | | Windward Islands v Jamaica |
| 04 Feb 1988 | Red Stripe Cup 1987/88 | | Windward Islands v Barbados |
| 25 Feb 1989 | Red Stripe Cup 1988/89 | | Windward Islands v Trinidad and Tobago |
| 11 Jan 1991 | Red Stripe Cup 1990/91 | | Windward Islands v Leeward Islands |
| 14 Feb 1992 | Red Stripe Cup 1991/92 | | Windward Islands v Trinidad and Tobago |
| 06 Mar 1992 | England A in West Indies and Bermuda 1991/92 | | Windward Islands v England A |
| 12 Feb 1993 | Red Stripe Cup 1992/93 | | Windward Islands v Barbados |
| 10 Apr 1993 | Pakistan in West Indies and Bermuda 1992/93 | | West Indies Under-23s v Pakistanis |
| 14 Jan 1994 | Red Stripe Cup 1993/94 | | Windward Islands v Guyana |
| 02 Apr 1994 | England in West Indies 1993/94 | | West Indies Board XI v England XI |
| 16 Feb 1996 | Red Stripe Cup 1995/96 | | Windward Islands v Trinidad and Tobago |
| 12 Apr 1996 | New Zealand in West Indies and Bermuda 1995/96 | | West Indies Board President's XI v New Zealanders |
| 08 Feb 1997 | Red Stripe Cup 1996/97 | | Windward Islands v Barbados |
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