Teams Rupert Scotland played for
| Main FC | Leeward Islands (1958) |
| Other FC | Bermuda (1971/72) |
| Miscellaneous | St George's Cricket Club (1959-1969/70) |
| Bermuda (1961-1972) | |
| Pond Hill Stars (1962) | |
| Bermuda Select XI (1964) | |
| Bermuda Board XI (1970/71) | |
| National Sports Club (1971) | |
| Bermuda Wanderers (1978-1985) |
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