Teams Winston Herbert played for
| Kent Cricket League | Barbados Overseas Cricket Association (2006) |
| Miscellaneous | Solihull Blossomfield (1988-1990) |
| Barbados (1988/89) | |
| Old Edwardians (1991-1993) | |
| Old Edwardians Second XI (1991) | |
| Barbados Overseas Cricket Association Second XI (2006) |
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