2008 winners - George Heriots F.P.
| Saturday 20th September | Sunday 21st September | Monday 22nd September |
| | 1st Round | 2nd Round | 3rd Round | Semi-Final | Final |
| 1. | Strathallians
Old Oundelians | Old Oundelians
(2-1)
Old Etonians
(3-0) | Old Etonians
(2½-½)
Lenzie Academicals
(2-1) | Lenzie Academicals
(2-1)
George Heriots
(2½-½) | George Heriots
(2-1)
Edinburgh Academicals
(2-1) |
| 2. | Old Fettesians
Old Etonians |
| 3. | Lenzie Academicals
Royal High School F.P. | Lenzie Academicals
(3-0)
Stewart's Melville
(2-1) |
| 4. | Daniel Stewart's/Melville F.P.
Hutchesons' G.S.F.P. |
| 5. | Old St Beghians
K C S Wimbledon | K C S Wimbledon
(2-1)
Old Grammarians
(2-1) | Old Grammarians
(2-1)
George Heriots
(2-1) |
| 6. | Old Grammarians
Aberdeen G.S.F.P. |
| 7. | Perth Academicals
George Heriots F.P. | George Heriots
(2-1)
Madras College
(2-1) |
| 8. | Dollar Academicals
Madras College |
| 9. | Old Reptonians
Hillhead High School F.P. | Hillhead High School
(2-1)
Gordonians
(2-1) | Gordonians
(3-0)
Watsonians
(2½-½) | Watsonians
(2½-½)
Edinburgh Academicals
(2-1) |
| 10. | Gordonians
Old Lorettonians |
| 11. | Watsonians
Morrisonians
(2-1) | Watsonians
(2½-½)
Old Cathusians
(2-1)
|
| 12. | Crieff High School F.P.
Old Carthusians |
| 13. | Merchistonians
Old Uppinghamians | Old Uppinghamians
(2½-½)
Edinburgh Academicals
(2-1) | Edinburgh Academicals
(2-1)
Breadalbane Academicals
(2-1) |
| 14. | Old Salopians
Edinburgh Academicals |
| 15. | Glasgow Academicals
Old Glenalmond | Glasgow Academicals
(2-1)
Breadalbane Academicals
(2-1) |
| 16. | Breadalbane Academicals
Glasgow High School F.P. |