| 13/09/08 | Motherwell FC Sutton 55, Clarkson 57 | 2-4 | Celtic Maloney 5, Samaras 9, 42, McDonald 24 |
| 13/09/08 | Rangers Boyd 58(p), 62 | 2-1 | Kilmarnock Wright 9 |
| 13/09/08 | Aberdeen McDonald 7 | 1-2 | Hamilton Graham 34, McCarthy 58 |
| 13/09/08 | Falkirk McCann 3, Arfield 90 | 2-1 | Hearts Stewart 71 |
| 13/09/08 | Hibernian Fletcher 22, 63 | 2-1 | Dundee United Wilkie 45 |
| 13/09/08 | Inverness Rooney 43(p) | 1-2 | St Mirren Mehmet 61, Brady 80 |
| 20/09/08 | Aberdeen | 0-1 | Dundee United Sandaza 47(p) |
| 20/09/08 | Hamilton | 0-1 | Hibernian Riordan 39 |
| 20/09/08 | Hearts Mikoliunas 8 | 1-0 | Inverness |
| 20/09/08 | St Mirren Mehmet 50(p) | 1-1 | Falkirk Barrett 47 |
| 21/09/08 | Rangers Davis 57, Novo 76 | 2-1 | Motherwell FC Clarkson 87 |
| 21/09/08 | Kilmarnock Taouil 89(p) | 1-3 | Celtic Maloney 26, Samaras 56, 82(p) |
| 27/09/08 | Celtic Vennegoor of Hesselink 14, 90, McDonald 78 | 3-2 | Aberdeen Mulgrew 57, 65 |
| 27/09/08 | Dundee United Conway 39, Daly 50, Robertson 61 | 3-0 | Hearts |
| 27/09/08 | Falkirk Lovell 44, Arfield 69, 87(p), O'Brien 72 | 4-1 | Hamilton Olejnik 90(o) |
| 27/09/08 | Inverness McGuire 21, Barrowman 43(p), Black 81 | 3-1 | Kilmarnock Sammon 4 |
| 27/09/08 | Motherwell FC Sutton 48, Malcolm 62 | 2-1 | St Mirren Mehmet 30 |
| 28/09/08 | Hibernian | 0-3 | Rangers Miller 31, 40, Bougherra 73 |
