| Year | Tournament | Result | Player | Age | Nation |
|---|---|---|---|---|---|
| 1998 | US Open | R128 | Mark Merklein | 26 | Bahamas |
| 1998 | Wimbledon | R128 | Mark Knowles | 26 | Bahamas |
| 1997 | Australian Open | R128 | Mark Knowles | 25 | Bahamas |
| 1996 | US Open | R64 | Mark Knowles | 24 | Bahamas |
| 1996 | Wimbledon | R64 | Mark Knowles | 24 | Bahamas |
| 1996 | French Open | R64 | Mark Knowles | 24 | Bahamas |
| 1995 | US Open | R128 | Mark Knowles | 23 | Bahamas |
| 1995 | Wimbledon | R64 | Mark Knowles | 23 | Bahamas |
| 1994 | US Open | R32 | Roger Smith | 30 | Bahamas |
| 1994 | US Open | R128 | Mark Merklein | 22 | Bahamas |
| 1994 | Wimbledon | R64 | Mark Knowles | 22 | Bahamas |
| 1994 | Australian Open | R128 | Roger Smith | 29 | Bahamas |
| 1994 | Australian Open | R128 | Mark Knowles | 22 | Bahamas |
| 1992 | Wimbledon | R64 | Mark Knowles | 20 | Bahamas |
| 1989 | Wimbledon | R128 | Roger Smith | 25 | Bahamas |
| 1989 | French Open | R128 | Roger Smith | 25 | Bahamas |
| 1989 | Australian Open | R128 | Roger Smith | 24 | Bahamas |
| 1988 | US Open | R128 | Roger Smith | 24 | Bahamas |
| 1988 | Australian Open | R128 | Roger Smith | 23 | Bahamas |
| 1987 | US Open | R64 | Roger Smith | 23 | Bahamas |
Open Era Grand Slam Tennis