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| Date | Venue | Team | Score | Res | Scorers | Read | |
| League | 31/08/08 | H | Kilmanahan Utd | 0-0 | D | Read | |
| League | 07/09/08 | A | St Nicholas | 6-2 | L | Glasheen(2) | Read |
| League | 21/09/08 | H | Moyglass Utd | 3-2 | W | Gibbons, McGuire & Davis | Read |
| League | 28/09/08 | A | Cashel Town | 0-5 | L | Read | |
| League | 05/09/08 | A | St Michaels B | 0-0 | D | Read | |
| League | 19/10/08 | A | Two Mile Borris | 2-0 | L | Read | |
| League | 02/11/08 | H | Wilderness Rovers | 0-0 | D | Read | |
| League | 23/11/08 | H | Two Mile Borris | 1-2 | L | Larkin | Read |
| League | 14/12/08 | A | Kilmanahan | 0-1 | W | O'Brien | Read |
| League | 04/01/09 | A | Galbally Utd | 3-1 | L | Gibbons | Read |
| Date | Venue | Team | Score | Res | Scorers | Read | |
| 1st | H | Dundrum FC | 4-0 | W | O'Brien(2), Moore & Gibbons | Read | |
| 2nd | A | Kilmanahan/Rock |
| Date | Venue | Team | Score | Res | Scorers | Read | |
| 1st | 24/08/08 | A | Wilderness Rovers | 2-1 | L | Kiely | Read |
| Date | Venue | Team | Score | Res | Scorers | Read | |
| 1st | Bye | ||||||
| 2nd | 21/12/08 | A | Clonmel Celtic B | 3-3 | W | OG, McGuire & Cronin (Town Win 5-4 On Penalties) | Read |
| 3rd |