| 1999-12-18 | PartickvStenhousemuirLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-12-04 | StenhousemuirvAlloaLeague One · Scotland | 1–3 | League One · Scotland |
| 1999-11-27 | ClydevStenhousemuirLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-11-20 | StranraervStenhousemuirLeague One · Scotland | 2–0 | League One · Scotland |
| 1999-11-10 | StenhousemuirvHamiltonLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-11-06 | ArbroathvStenhousemuirLeague One · Scotland | 0–3 | League One · Scotland |
| 1999-10-30 | StenhousemuirvQueen of SthLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-10-23 | StenhousemuirvPartickLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-10-15 | StirlingvStenhousemuirLeague One · Scotland | 5–1 | League One · Scotland |
| 1999-10-02 | StenhousemuirvClydeLeague One · Scotland | 1–3 | League One · Scotland |
| 1999-09-25 | AlloavStenhousemuirLeague One · Scotland | 1–4 | League One · Scotland |
| 1999-09-18 | StenhousemuirvArbroathLeague One · Scotland | 1–3 | League One · Scotland |
| 1999-09-11 | Queen of SthvStenhousemuirLeague One · Scotland | 0–3 | League One · Scotland |
| 1999-09-05 | HamiltonvStenhousemuirLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-08-28 | StenhousemuirvStranraerLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-08-21 | Ross CountyvStenhousemuirLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-08-14 | StenhousemuirvStirlingLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-08-07 | PartickvStenhousemuirLeague One · Scotland | 0–1 | League One · Scotland |