| 1999-12-27 | StranraervClydeLeague One · Scotland | 2–2 | League One · Scotland |
| 1999-12-18 | StirlingvStranraerLeague One · Scotland | 2–5 | League One · Scotland |
| 1999-12-04 | StranraervArbroathLeague One · Scotland | 2–2 | League One · Scotland |
| 1999-11-27 | AlloavStranraerLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-11-20 | StranraervStenhousemuirLeague One · Scotland | 2–0 | League One · Scotland |
| 1999-11-14 | PartickvStranraerLeague One · Scotland | 2–0 | League One · Scotland |
| 1999-11-06 | Queen of SthvStranraerLeague One · Scotland | 0–5 | League One · Scotland |
| 1999-10-30 | StranraervHamiltonLeague One · Scotland | 0–2 | League One · Scotland |
| 1999-10-23 | StranraervStirlingLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-10-15 | Ross CountyvStranraerLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-10-02 | StranraervAlloaLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-09-25 | ArbroathvStranraerLeague One · Scotland | 1–2 | League One · Scotland |
| 1999-09-18 | StranraervQueen of SthLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-09-11 | HamiltonvStranraerLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-09-04 | StranraervPartickLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-08-28 | StenhousemuirvStranraerLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-08-21 | ClydevStranraerLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-08-14 | StranraervRoss CountyLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-08-07 | StirlingvStranraerLeague One · Scotland | 1–1 | League One · Scotland |