| 09 Oct 21 | r16        | The SpartansThe Spartans | 1 - 2 | Bonnyrigg Rose AthleticBonnyrigg Ros |
| 09 Oct 21 | r16        | Berwick RangersBerwick Range | 11 - 0 | Vale of LeithenVale of Leith |
| 09 Oct 21 | r16        | BroomhillBroomhill | 2 - 0 | Dalbeattie StarDalbeattie St |
| 09 Oct 21 | r16        | Celtic BCeltic B | 1 - 0 | Gretna 2008Gretna 2008 |
| 09 Oct 21 | r16        | Cumbernauld ColtsCumbernauld C | 4 - 1 | Boness UnitedBoness United |
| 09 Oct 21 | r16        | East StirlingshireEast Stirling | 2 - 0 | Edinburgh UniversityEdinburgh Uni |
| 09 Oct 21 | r16        | Gala Fairydean RoversGala Fairydea | 2 - 3 | Civil Service StrollersCivil Service |
| 09 Oct 21 | r16        | University of StirlingUniversity of | 0 - 3 | East KilbrideEast Kilbride |
| 23 Oct 21 | r16        | Rangers BRangers B | 3 - 1 | Caledonian BravesCaledonian Br |