| ROUND | R1 | R2 | R3 | QF | SF | F |
| Season archive |
| Tuesday, 25 August 2009 | ||||||
| r2 | Alloa Athletic | 0-2 | Dundee United | |||
| 23 | Shala | |||||
| 39 | Goodwillie | |||||
| r2 | Forfar Athletic | 2-4 | Dundee | |||
| 55 | Tulloch | 11 | Griffiths | |||
| 72 | Campbell | 15 | Antoine-Curier | |||
| 31 | Antoine-Curier | |||||
| 67(og) | Tod | |||||
| r2 | Inverness CT | 4-0 | Albion Rovers | |||
| 8 | Eagle | |||||
| 16 | Rooney | |||||
| 41 | Bulvītis | |||||
| 57 | Munro | |||||
| r2 | Kilmarnock | 3-1 | Morton | |||
| 24(p) | Sammon | 44(p) | McGuffie | |||
| 64 | Sammon | |||||
| 90 | Kyle | |||||
| r2 | Partick Thistle | 1-2 | Queen of the South | |||
| 30 | Donnelly | 64 | Weatherston | |||
| 90 | Weatherston | |||||
| r2 | Ross County | 2-1 | Hamilton | |||
| 32 | Di Giacomo | 90 | Mensing | |||
| 53 | Brittain | |||||
| Wednesday, 26 August 2009 | ||||||
| r2 | Arbroath | 0-6 | St.Johnstone | |||
| 24 | Milne | |||||
| 27 | Morais | |||||
| 42 | Deuchar | |||||
| 45 | Milne | |||||
| 67 | Deuchar | |||||
| 71 | Samuel | |||||
| r2 | Ayr United | 0-2 | St.Mirren | |||
| 25 | Higdon | |||||
| 90 | Mehmet | |||||
| r2 | Dunfermline | 3-1 | Raith Rovers | |||
| 38 | Kirk | 50(p) | Williamson | |||
| 52(og) | Campbell | |||||
| 68 | Kirk | |||||
| r2 | Hibernian | 3-0 | Brechin City | |||
| 10(og) | Nimmo | |||||
| 16 | Riordan | |||||
| 55 | Hanlon | |||||
| 6 | +1 | Billy MEHMET (St.Mirren) |
| 4 | +2 | Kenny DEUCHAR (St.Johnstone) |
| +2 | Andy KIRK (Dunfermline) | |
| 3 | +2 | Steve MILNE (St.Johnstone) |
| +1 | Collin SAMUEL (St.Johnstone) | |
| 2 | +1 | Ross CAMPBELL (Forfar Athletic) |
| +1 | Adam ROONEY (Inverness CT) | |
| +1 | Robert EAGLE (Inverness CT) | |
| +2 | David WEATHERSTON (Queen of the South) | |
| +1 | Leigh GRIFFITHS (Dundee, 1p) | |
| Barry WILSON (Queen of the South) | ||
| Michael GARDYNE (Ross County) | ||
| +2 | Mickaël ANTOINE-CURIER (Dundee) | |
| Andy RODGERS (East Stirlingshire) | ||
| Chris ERSKINE (Partick Thistle) | ||
| Liam BUCHANAN (Partick Thistle, 1p) | ||
| Rory McALLISTER (Brechin City) | ||
| +2 | Conor SAMMON (Kilmarnock, 1p) | |
| Peter WEATHERSON (Morton) | ||
| +1 | Iain WILLIAMSON (Raith Rovers, 1p) |