1999/00 Real San Domingo season
Islands League
| Pos | P | W | D | L | GF | GA | GD | Pts |
|---|---|---|---|---|---|---|---|---|
| 7 | 34 | 16 | 9 | 9 | 56 | 45 | +11 | 57 |
FA Cup
| Round / date | Home | Score | Away |
|---|---|---|---|
| First Round | Rocastle United | 1–0 | Real San Domingo |
Brados Cup
| Round / date | Home | Score | Away |
|---|---|---|---|
| First Round | Real San Domingo | 3–0 | South Bay Sports |
| Second Round | Real San Domingo | 1–0 | AFC Droy |
| Quarter-Finals | Adelaide Wanderers | 1–1 | Real San Domingo |