| 09/08/08 | Falkirk | 0-1 | Rangers Velicka 64 |
| 09/08/08 | Hearts Stewart 25, Ksanavicius 40, Mikoliunas 82 | 3-2 | Motherwell Clarkson 33, 81 |
| 09/08/08 | Kilmarnock Hamill 80 | 1-0 | Hibernian |
| 09/08/08 | Aberdeen | 0-2 | Inverness Barrowman 27, McBain 90 |
| 10/08/08 | Celtic Robson 62(p) | 1-0 | St Mirren |
| 11/08/08 | Hamilton Stevenson 29, McArthur 39, Graham 63 | 3-1 | Dundee United McLaughlin 23(o) |
| 16/08/08 | Hibernian Nish 1, 25, Hanlon 47 | 3-2 | Falkirk Higdon 30, 53 |
| 16/08/08 | Inverness | 0-1 | Hamilton Offiong 45 |
| 16/08/08 | Motherwell | 0-1 | Aberdeen Mulgrew 86 |
| 16/08/08 | Rangers Lafferty 37, Boyd 90(p) | 2-0 | Hearts |
| 16/08/08 | St Mirren | 0-0 | Kilmarnock |
| 17/08/08 | Dundee United Sandaza 79 | 1-1 | Celtic Hartley 51 |
| 23/08/08 | Aberdeen Young 45 | 1-1 | Rangers Weir 24 |
| 23/08/08 | Celtic McManus 32, Samaras 44, 68 | 3-0 | Falkirk |
| 23/08/08 | Hearts Mole 45, Stewart 75(p) | 2-1 | St Mirren Mehmet 70 |
| 23/08/08 | Inverness Cowie 21 | 1-1 | Hibernian Nish 46 |
| 23/08/08 | Kilmarnock Pascali 45 | 1-0 | Hamilton |
| 23/08/08 | Motherwell Sutton 34 | 1-1 | Dundee United Wilkie 40 |
| 30/08/08 | Dundee United | 0-2 | Kilmarnock Skelton 40, Invincibile 59 |
| 30/08/08 | Falkirk Stewart 60 | 1-2 | Inverness Cowie 68, Imrie 85 |
| 30/08/08 | Hamilton Lyle 80 | 1-2 | Hearts Zaliukas 18, Driver 59 |
| 30/08/08 | Hibernian | 0-1 | Motherwell Sutton 79 |
| 30/08/08 | St Mirren | 0-1 | Aberdeen Mackie 43 |
| 31/08/08 | Celtic Samaras 39, Nakamura 90 | 2-4 | Rangers Cousin 37, Miller 52, 79, Pedro Mendes 62 |
