Season 1999/2000 Fixture List
| Sat | Jul 31 | Hibernian | A | 2-2 |
| Sat | Aug 7 | Dundee United | H | 2-2 |
| Sun | Aug 15 | Rangers | A | 1-4 |
| Wed | Aug 18 | Raith Rovers (League Cup 2) | A | 2-2 |
| Sat | Aug 21 | Kilmarnock | A | 1-0 |
| Sat | Aug 28 | Dundee | H | 0-2 |
| Sat | Sep 11 | St Johnstone | A | 1-1 |
| Tue | Oct 12 | Inverness CT (League Cup 3) | A | 1-0 |
| Sat | Oct 16 | Hibernian | H | 2-2 |
| Wed | Oct 20 | Aberdeen | H | 5-6 |
| Sat | Oct 23 | Dundee United | A | 2-0 |
| Wed | Oct 27 | Celtic | A | 1-0 |
| Sat | Oct 30 | St Johnstone | H | 1-0 |
| Sat | Nov 6 | Hearts | A | 1-1 |
| Sat | Nov 20 | Dundee | A | 1-0 |
| Tue | Nov 23 | Hearts | H | 2-1 |
| Sun | Nov 28 | Celtic | H | 3-2 |
| Wed | Dec 1 | Dundee United | A | 2-3 |
| Sat | Dec 11 | Hibernian | A | 2-2 |
| Sat | Dec 18 | Rangers | H | 1-5 |
| Sat | Jan 22 | St Johnstone | A | 1-1 |
| Wed | Jan 26 | Aberdeen | A | 1-1 |
| Tue | Feb 1 | Arbroath (Scottish Cup 3) | A | 1-1 |
| Sat | Feb 5 | Dundee | H | 0-3 |
| Sat | Feb 12 | Kilmarnock | A | 2-0 |
| Sat | Feb 19 | Arbroath (Cup Replay) | H | 2-2 |
| Tue | Feb 22 | Kilmarnock | H | 0-4 |
| Sat | Feb 26 | Ayr Utd (Scottish Cup 4) | H | 3-4 |
| Wed | Mar 1 | Hearts | H | 0-2 |
| Sat | Mar 4 | Aberdeen | H | 1-0 |
| Sat | Mar 18 | Rangers | A | 2-6 |
| Tue | Mar 21 | IFK Gothenburg (friendly) | H | 0-0 |
| Sat | Mar 25 | Hearts | A | 0-0 |
| Sat | Apr 1 | St Johnstone | H | 2-1 |
| Wed | Apr 5 | Celtic | A | 0-4 |
| Sat | Apr 8 | Dundee | A | 1-4 |
| Sun | Apr 16 | Kilmarnock (SKY) | H | 2-0 |
| Wed | Apr 19 | Dundee United | H | 1-3 |
| Sat | Apr 22 | Aberdeen | A | 1-2 |
| Sat | Apr 29 | Celtic | H | 1-1 |
| Sat | May 6 | Hibernian | H | 2-0 |
| Sat | May 13 | Dundee United | A | 2-1 |
| Sun | May 21 | Rangers | H | 2-0 |