| 1999-12-27 | StranraervClydeLeague One · Scotland | 2–2 | League One · Scotland |
| 1999-12-18 | ClydevAlloaLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-12-04 | HamiltonvClydeLeague One · Scotland | 2–3 | League One · Scotland |
| 1999-11-27 | ClydevStenhousemuirLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-11-20 | StirlingvClydeLeague One · Scotland | 1–2 | League One · Scotland |
| 1999-11-09 | ClydevQueen of SthLeague One · Scotland | 3–0 | League One · Scotland |
| 1999-11-06 | ClydevRoss CountyLeague One · Scotland | 3–1 | League One · Scotland |
| 1999-10-30 | PartickvClydeLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-10-23 | AlloavClydeLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-10-15 | ClydevArbroathLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-10-02 | StenhousemuirvClydeLeague One · Scotland | 1–3 | League One · Scotland |
| 1999-09-25 | ClydevHamiltonLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-09-18 | Ross CountyvClydeLeague One · Scotland | 2–0 | League One · Scotland |
| 1999-09-11 | ClydevPartickLeague One · Scotland | 2–0 | League One · Scotland |
| 1999-09-04 | Queen of SthvClydeLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-08-28 | ClydevStirlingLeague One · Scotland | 3–0 | League One · Scotland |
| 1999-08-21 | ClydevStranraerLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-08-14 | ArbroathvClydeLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-08-07 | ClydevAlloaLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-05-08 | East FifevClydeLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-05-01 | ClydevStirlingLeague One · Scotland | 4–1 | League One · Scotland |
| 1999-04-24 | Queen of SthvClydeLeague One · Scotland | 2–1 | League One · Scotland |
| 1999-04-17 | ClydevAlloaLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-04-10 | LivingstonvClydeLeague One · Scotland | 2–0 | League One · Scotland |
| 1999-04-03 | Inverness CvClydeLeague One · Scotland | 3–0 | League One · Scotland |
| 1999-03-20 | ClydevArbroathLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-03-13 | PartickvClydeLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-03-06 | ClydevForfarLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-02-27 | StirlingvClydeLeague One · Scotland | 2–3 | League One · Scotland |
| 1999-02-20 | ClydevEast FifeLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-02-16 | AlloavClydeLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-02-06 | ClydevLivingstonLeague One · Scotland | 0–3 | League One · Scotland |
| 1999-02-02 | ForfarvClydeLeague One · Scotland | 3–1 | League One · Scotland |
| 1999-01-30 | ArbroathvClydeLeague One · Scotland | 0–3 | League One · Scotland |
| 1999-01-16 | ClydevInverness CLeague One · Scotland | 1–1 | League One · Scotland |