| 1999-12-27 | HamiltonvStirlingLeague One · Scotland | 0–2 | League One · Scotland |
| 1999-12-18 | StirlingvStranraerLeague One · Scotland | 2–5 | League One · Scotland |
| 1999-12-11 | StirlingvQueen of SthLeague One · Scotland | 3–0 | League One · Scotland |
| 1999-11-27 | PartickvStirlingLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-11-20 | StirlingvClydeLeague One · Scotland | 1–2 | League One · Scotland |
| 1999-11-12 | Ross CountyvStirlingLeague One · Scotland | 1–3 | League One · Scotland |
| 1999-11-06 | AlloavStirlingLeague One · Scotland | 4–4 | League One · Scotland |
| 1999-10-30 | StirlingvArbroathLeague One · Scotland | 3–4 | League One · Scotland |
| 1999-10-23 | StranraervStirlingLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-10-15 | StirlingvStenhousemuirLeague One · Scotland | 5–1 | League One · Scotland |
| 1999-10-02 | StirlingvPartickLeague One · Scotland | 3–1 | League One · Scotland |
| 1999-09-25 | Queen of SthvStirlingLeague One · Scotland | 3–3 | League One · Scotland |
| 1999-09-18 | StirlingvAlloaLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-09-11 | ArbroathvStirlingLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-09-04 | StirlingvRoss CountyLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-08-28 | ClydevStirlingLeague One · Scotland | 3–0 | League One · Scotland |
| 1999-08-21 | StirlingvHamiltonLeague One · Scotland | 2–0 | League One · Scotland |
| 1999-08-14 | StenhousemuirvStirlingLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-08-07 | StirlingvStranraerLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-05-08 | StirlingvArbroathLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-05-01 | ClydevStirlingLeague One · Scotland | 4–1 | League One · Scotland |
| 1999-04-24 | StirlingvLivingstonLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-04-17 | StirlingvPartickLeague One · Scotland | 3–0 | League One · Scotland |
| 1999-04-10 | Inverness CvStirlingLeague One · Scotland | 2–2 | League One · Scotland |
| 1999-04-03 | StirlingvForfarLeague One · Scotland | 2–2 | League One · Scotland |
| 1999-03-20 | East FifevStirlingLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-03-13 | StirlingvAlloaLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-03-06 | Queen of SthvStirlingLeague One · Scotland | 3–0 | League One · Scotland |
| 1999-02-27 | StirlingvClydeLeague One · Scotland | 2–3 | League One · Scotland |
| 1999-02-20 | ArbroathvStirlingLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-02-17 | PartickvStirlingLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-02-06 | StirlingvInverness CLeague One · Scotland | 1–5 | League One · Scotland |
| 1999-01-30 | StirlingvEast FifeLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-01-26 | StirlingvQueen of SthLeague One · Scotland | 1–3 | League One · Scotland |
| 1999-01-16 | ForfarvStirlingLeague One · Scotland | 3–3 | League One · Scotland |