| 30 May 2004 | Coronel Scottish Cup 2004 | First Round | Hillhead High School Former Pupils v Stirling County |
| 06 May 2001 | Scottish Cup 2001 | Section 1 | Hillhead High School Former Pupils v West of Scotland |
| 13 May 2001 | Scottish Cup 2001 | Section 1 | Hillhead High School Former Pupils v Aberdeenshire |
| 22 Jun 2003 | Coronel Scottish Cup 2003 | Second Round | Hillhead High School Former Pupils v Dunfermline |
| 29 May 2011 | Scottish Cup 2011 | First Round | Hillhead High School Former Pupils v Stenhousemuir |
| 18 Jun 2000 | Scottish Cup 2000 | Section Three | Hillhead High School Former Pupils v Dunfermline |
| 18 May 1997 | Whyte and Mackay Scottish Cup 1997 | Preliminary Round Section 1 | Hillhead High School Former Pupils v Strathmore |
| 15 Jun 1997 | Whyte and Mackay Scottish Cup 1997 | Preliminary Round Section 1 | Hillhead High School Former Pupils v Stirling County |
| 28 May 1995 | Whyte and Mackay Scottish Cup 1995 | Preliminary Round Section 4 | Hillhead High School Former Pupils v Aberdeenshire |
| 09 Jul 1995 | Whyte and Mackay Scottish Cup 1995 | Preliminary Round Section 4 | Hillhead High School Former Pupils v Inverurie |
| 18 Jul 1993 | Whyte and Mackay Scottish Cup 1993 | Preliminary Round Section 5 | Hillhead High School Former Pupils v Carlton |
| 05 Jul 1992 | Whyte and Mackay Scottish Cup 1992 | Preliminary Round Section 8 | Hillhead High School Former Pupils v Kelso |
| 04 Jul 1999 | Scottish Cup 1999 | Preliminary Round Section 3 | Hillhead High School Former Pupils v Ayr |
| 27 Jun 1999 | Scottish Cup 1999 | Preliminary Round Section 3 | Hillhead High School Former Pupils v St Michael's |
| 13 Jun 1999 | Scottish Cup 1999 | Preliminary Round Section 3 | Hillhead High School Former Pupils v Carlton |
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