| 1999-02-16 | ForfarvEast FifeLeague One · Scotland | 2–4 | League One · Scotland |
| 1999-02-13 | Inverness CvQueen of SthLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-02-06 | ArbroathvAlloaLeague One · Scotland | 1–2 | League One · Scotland |
| 1999-02-06 | StirlingvInverness CLeague One · Scotland | 1–5 | League One · Scotland |
| 1999-02-06 | Queen of SthvForfarLeague One · Scotland | 0–3 | League One · Scotland |
| 1999-02-06 | East FifevPartickLeague 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 | StirlingvEast FifeLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-01-30 | Inverness CvForfarLeague One · Scotland | 2–0 | League One · Scotland |
| 1999-01-30 | LivingstonvPartickLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-01-30 | ArbroathvClydeLeague One · Scotland | 0–3 | League One · Scotland |
| 1999-01-30 | Queen of SthvAlloaLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-01-26 | StirlingvQueen of SthLeague One · Scotland | 1–3 | League One · Scotland |
| 1999-01-20 | LivingstonvEast FifeLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-01-19 | ArbroathvForfarLeague One · Scotland | 2–2 | League One · Scotland |
| 1999-01-17 | East FifevQueen of SthLeague One · Scotland | 0–1 | League One · Scotland |
| 1999-01-16 | PartickvArbroathLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-01-16 | ClydevInverness CLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-01-16 | ForfarvStirlingLeague One · Scotland | 3–3 | 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 |
| 1999-01-09 | Inverness CvArbroathLeague One · Scotland | 2–0 | League One · Scotland |