Glasgow Rangers 
| 1999-07-31 | Premiership | Kilmarnock FC | (H) | 2 | - 1 | W | |
| 1999-08-07 | Premiership | Heart of Midlothian FC | (A) | 4 | - 0 | W | |
| 1999-08-15 | Premiership | Motherwell FC | (H) | 4 | - 1 | W | |
| 1999-08-21 | Premiership | Dundee United FC | (H) | 4 | - 1 | W | |
| 1999-08-28 | Premiership | Hibernian FC | (A) | 1 | - 0 | W | |
| 1999-09-11 | Premiership | Aberdeen FC | (H) | 3 | - 0 | W | |
| 1999-09-25 | Premiership | St.Johnstone FC | (H) | 3 | - 1 | W | |
| 1999-10-02 | Premiership | Dundee FC | (A) | 3 | - 2 | W | |
| 1999-10-16 | Premiership | Kilmarnock FC | (A) | 1 | - 1 | D | |
| 1999-10-30 | Premiership | Aberdeen FC | (A) | 5 | - 1 | W | |
| 1999-11-07 | Premiership | Celtic FC | (H) | 4 | - 2 | W | |
| 1999-11-20 | Premiership | Hibernian FC | (H) | 2 | - 0 | W | |
| 1999-11-28 | Premiership | Dundee FC | (H) | 1 | - 2 | L | |
| 1999-12-11 | Premiership | Kilmarnock FC | (H) | 1 | - 0 | W | |
| 1999-12-18 | Premiership | Motherwell FC | (A) | 5 | - 1 | W | |
| 1999-12-22 | Premiership | Heart of Midlothian FC | (H) | 1 | - 0 | W | |
| 1999-12-27 | Premiership | Celtic FC | (A) | 1 | - 1 | D | |
| 2000-01-22 | Premiership | Aberdeen FC | (H) | 5 | - 0 | W | |
| 2000-02-02 | Premiership | Dundee United FC | (A) | 4 | - 0 | W | |
| 2000-02-06 | Premiership | Hibernian FC | (A) | 2 | - 2 | D | |
| 2000-02-15 | Premiership | St.Johnstone FC | (A) | 1 | - 1 | D | |
| 2000-02-27 | Premiership | Dundee FC | (A) | 7 | - 1 | W | |
| 2000-03-04 | Premiership | St.Johnstone FC | (H) | 0 | - 0 | D | |
| 2000-03-08 | Premiership | Celtic FC | (A) | 1 | - 0 | W | |
| 2000-03-18 | Premiership | Motherwell FC | (H) | 6 | - 2 | W | |
| 2000-03-26 | Premiership | Celtic FC | (H) | 4 | - 0 | W | |
| 2000-04-01 | Premiership | Aberdeen FC | (A) | 1 | - 1 | D | |
| 2000-04-04 | Premiership | Dundee United FC | (H) | 3 | - 0 | W | |
| 2000-04-12 | Premiership | Heart of Midlothian FC | (A) | 2 | - 1 | W | |
| 2000-04-15 | Premiership | Dundee United FC | (A) | 2 | - 0 | W | |
| 2000-04-23 | Premiership | St.Johnstone FC | (A) | 2 | - 0 | W | |
| 2000-04-30 | Premiership | Dundee FC | (H) | 3 | - 0 | W | |
| 2000-05-03 | Premiership | Hibernian FC | (H) | 5 | - 2 | W | |
| 2000-05-07 | Premiership | Kilmarnock FC | (A) | 2 | - 0 | W | |
| 2000-05-13 | Premiership | Heart of Midlothian FC | (H) | 1 | - 0 | W | |
| 2000-05-21 | Premiership | Motherwell FC | (A) | 0 | - 2 | L |