Scottish Challenge Cup competition results from 2005/2006
A full listing of matches played in the competition throughout the season
| 2nd Round |
| Tuesday, 30th August 2005 |
| Brechin City (SCD1) | 0 | Greenock Morton (SCD2) | 2 | 617 |
| Dundee (SCD1) | 1 | Airdrie United (SCD1) | 1 | 1,857 |
| after extra time, 90 minutes 1-1, Dundee won 3-2 on penalties |
| Partick Thistle (SCD2) | 4 | St. Johnstone (SCD1) | 4 | 1,466 |
| after extra time, 90 minutes 2-2, St Johnstone won 8-7 on penalties |
| Raith Rovers (SCD2) | 2 | Dumbarton (SCD2) | 1 | 1,382 |
| after extra time, 90 minutes 0-0 |
| Ross County (SCD1) | 0 | Hamilton Academical (SCD1) | 1 | 1,024 |
| Wednesday, 31st August 2005 |
| Queen of the South (SCD1) | 1 | St. Mirren (SCD1) | 2 | 1,415 |
| Stirling Albion (SCD2) | 2 | Berwick Rangers (SCD3) | 1 | 467 |
| Stranraer (SCD1) | 1 | Stenhousemuir (SCD3) | 2 | 412 |
| 1st Round |
| Saturday, 30th July 2005 |
| Arbroath (SCD3) | 1 | Stranraer (SCD1) | 3 | 319 |
| Ayr United (SCD2) | 0 | Stirling Albion (SCD2) | 1 | 910 |
| after extra time, 90 minutes 0-0 |
| Brechin City (SCD1) | 3 | Clyde (SCD1) | 2 | 547 |
| after extra time, 90 minutes 2-2 |
| East Fife (SCD3) | 0 | Stenhousemuir (SCD3) | 4 | 310 |
| Greenock Morton (SCD2) | 3 | Gretna (SCD2) | 2 | 2,798 |
| after extra time, 90 minutes 1-1 |
| Partick Thistle (SCD2) | 2 | Cowdenbeath (SCD3) | 0 | 1,541 |
| Peterhead (SCD2) | 1 | Berwick Rangers (SCD3) | 2 | 620 |
| after extra time, 90 minutes 1-1 |
| Queen of the South (SCD1) | 4 | Albion Rovers (SCD3) | 0 | 1,492 |
| Queen's Park (SCD3) | 0 | Hamilton Academical (SCD1) | 3 | 755 |
| Raith Rovers (SCD2) | 3 | Elgin City (SCD3) | 1 | 1,418 |
| after extra time, 90 minutes 1-1 |
| Ross County (SCD1) | 2 | Montrose (SCD3) | 1 | 1,200 |
| St. Johnstone (SCD1) | 2 | Alloa Athletic (SCD2) | 0 | 1,592 |
| St. Mirren (SCD1) | 1 | Forfar Athletic (SCD2) | 0 | 1,605 |
| after extra time, 90 minutes 0-0 |
| Sunday, 31st July 2005 |
| Dundee (SCD1) | 2 | East Stirlingshire (SCD3) | 0 | 2,554 |
