| 1999-12-27 | FalkirkvLivingstonChampionship · Scotland | 2–3 | Championship · Scotland |
| 1999-12-14 | AirdrievLivingstonChampionship · Scotland | 2–3 | Championship · Scotland |
| 1999-12-04 | ClydebankvLivingstonChampionship · Scotland | 1–5 | Championship · Scotland |
| 1999-11-27 | LivingstonvSt MirrenChampionship · Scotland | 1–2 | Championship · Scotland |
| 1999-11-20 | LivingstonvMortonChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-11-14 | DunfermlinevLivingstonChampionship · Scotland | 3–0 | Championship · Scotland |
| 1999-11-06 | Inverness CvLivingstonChampionship · Scotland | 2–0 | Championship · Scotland |
| 1999-10-30 | LivingstonvFalkirkChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-10-23 | Raith RvsvLivingstonChampionship · Scotland | 3–1 | Championship · Scotland |
| 1999-10-16 | LivingstonvAyrChampionship · Scotland | 4–1 | Championship · Scotland |
| 1999-10-02 | St MirrenvLivingstonChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-09-25 | LivingstonvClydebankChampionship · Scotland | 2–1 | Championship · Scotland |
| 1999-09-18 | LivingstonvInverness CChampionship · Scotland | 2–2 | Championship · Scotland |
| 1999-09-11 | FalkirkvLivingstonChampionship · Scotland | 0–2 | Championship · Scotland |
| 1999-09-04 | LivingstonvDunfermlineChampionship · Scotland | 0–1 | Championship · Scotland |
| 1999-08-28 | MortonvLivingstonChampionship · Scotland | 2–2 | Championship · Scotland |
| 1999-08-21 | LivingstonvAirdrieChampionship · Scotland | 3–0 | Championship · Scotland |
| 1999-08-14 | AyrvLivingstonChampionship · Scotland | 1–2 | Championship · Scotland |
| 1999-08-07 | LivingstonvRaith RvsChampionship · Scotland | 1–1 | Championship · Scotland |
| 1999-05-08 | ForfarvLivingstonLeague One · Scotland | 1–2 | League One · Scotland |
| 1999-05-01 | LivingstonvInverness CLeague One · Scotland | 4–3 | League One · Scotland |
| 1999-04-24 | StirlingvLivingstonLeague One · Scotland | 0–0 | League One · Scotland |
| 1999-04-17 | ArbroathvLivingstonLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-04-10 | LivingstonvClydeLeague One · Scotland | 2–0 | League One · Scotland |
| 1999-04-03 | LivingstonvAlloaLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-03-20 | PartickvLivingstonLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-03-13 | LivingstonvQueen of SthLeague One · Scotland | 1–2 | League One · Scotland |
| 1999-03-06 | East FifevLivingstonLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-02-27 | Inverness CvLivingstonLeague One · Scotland | 3–1 | League One · Scotland |
| 1999-02-20 | LivingstonvForfarLeague One · Scotland | 3–0 | League One · Scotland |
| 1999-02-16 | LivingstonvArbroathLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-02-06 | ClydevLivingstonLeague One · Scotland | 0–3 | League One · Scotland |
| 1999-01-30 | LivingstonvPartickLeague One · Scotland | 1–1 | League One · Scotland |
| 1999-01-20 | LivingstonvEast FifeLeague One · Scotland | 1–0 | League One · Scotland |
| 1999-01-16 | AlloavLivingstonLeague One · Scotland | 1–3 | League One · Scotland |