| 1999-12-18 | ClydevAlloaLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-12-04 | StenhousemuirvAlloaLeague One · Scotland | 1–3 | League One · Scotland |
| 1999-11-27 | AlloavStranraerLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-11-16 | HamiltonvAlloaLeague One · Scotland | 1–2 | League One · Scotland |
| 1999-11-09 | AlloavArbroathLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-11-06 | AlloavStirlingLeague One · Scotland | 4–4 | League One · Scotland |
| 1999-10-30 | Ross CountyvAlloaLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-10-23 | AlloavClydeLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-10-15 | PartickvAlloaLeague One · Scotland | 2–2 | League One · Scotland |
| 1999-10-02 | StranraervAlloaLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-09-25 | AlloavStenhousemuirLeague One · Scotland | 1–4 | League One · Scotland |
| 1999-09-18 | StirlingvAlloaLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-09-11 | AlloavRoss CountyLeague One · Scotland | 2–0 | League One · Scotland |
| 1999-09-04 | ArbroathvAlloaLeague One · Scotland | 2–2 | League One · Scotland |
| 1999-08-28 | AlloavHamiltonLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-08-21 | Queen of SthvAlloaLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-08-14 | AlloavPartickLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-08-07 | ClydevAlloaLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-05-08 | Inverness CvAlloaLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-05-01 | AlloavEast FifeLeague One · Scotland | 3–1 | League One · Scotland |
| 1999-04-24 | ForfarvAlloaLeague One · Scotland | 3–1 | League One · Scotland |
| 1999-04-17 | ClydevAlloaLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-04-10 | AlloavArbroathLeague One · Scotland | 1–2 | League One · Scotland |
| 1999-04-03 | LivingstonvAlloaLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-03-20 | AlloavQueen of SthLeague One · Scotland | 3–5 | League One · Scotland |
| 1999-03-13 | StirlingvAlloaLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-03-06 | AlloavPartickLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-02-27 | East FifevAlloaLeague One · Scotland | 0–4 | League One · Scotland |
| 1999-02-20 | AlloavInverness CLeague One · Scotland | 1–4 | League One · Scotland |
| 1999-02-16 | AlloavClydeLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-02-06 | ArbroathvAlloaLeague One · Scotland | 1–2 | League One · Scotland |
| 1999-01-30 | Queen of SthvAlloaLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-01-16 | AlloavLivingstonLeague One · Scotland | 1–3 | League One · Scotland |
| 1999-01-13 | PartickvAlloaLeague One · Scotland | 2–1 | League One · Scotland |