| U16 Citizen Cup | ||||||||
| Fixture No. | Date | Round | Home Club | Score | Score | Away Club | Match No. | |
| 4168 | 14-Sep-2008 | R1 | Bromham Youth | 8 | vs | 1 | Newport Pagnell Youth | 1 |
| 4169 | 14-Sep-2008 | R1 | Newport Pagnell Town | 4 | vs | 0 | Heath Panthers | 2 |
| 4170 | 16-Nov-2008 | R2 | Newport Pagnell Town | 5 | vs | 0 | Heath Panthers Hawks | 3 |
| 4171 | 09-Nov-2008 | R2 | Milton Keynes City | 3 | vs | 2 | Wing Raiders | 4 |
| 4172 | 16-Nov-2008 | R2 | Southside United Strikers | 6 | vs | 2 | Winslow United Pumas | 5 |
| 4173 | 16-Nov-2008 | R2 | Willen Rangers | R | vs | R | Southside United Scorpions | 6 |
| 4174 | 09-Nov-2008 | R2 | Willen Juniors A | 4 | vs | 5 | Halse United | 7 |
| 4175 | 19-Nov-2008 | R2 | Winslow United Tigers | 8 | vs | 2 | Wicken Rangers | 8 |
| 4176 | 09-Nov-2008 | R2 | Cranfield Colts | 10 | vs | 2 | Hanslope Hornets | 9 |
| 4177 | 23-Nov-2008 | R2 | Brackley Town | 8 | vs | 0 | Woburn Lions | 10 |
| 4178 | 09-Nov-2008 | R2 | Stony Stratford Town | 3 | vs | 1 | Bromham Youth | 11 |
| 4179 | 16-Nov-2008 | R2 | Water Eaton Youth | 1 | vs | 2 | Willen Juniors Warriors | 12 |
| 4180 | 07-Dec-2008 | R2 | Brackley Athletic | vs | City Colts | 13 | ||
| 4181 | 09-Nov-2008 | R2 | Newton Longville | 0 | vs | 6 | Emberton Athletic | 14 |
| 4182 | 16-Nov-2008 | R2 | Heelands Rangers | 2 | vs | 3 | Wolverton Tigermoths | 15 |
| 4183 | 09-Nov-2008 | R2 | Scot Youth | 3 | vs | 0 | MK Wanderers B | 16 |
| 4184 | 16-Nov-2008 | R2 | MK Wanderers A | 6 | vs | 1 | Wootton Rangers | 17 |
| 4185 | 23-Nov-2008 | R2 | Two Mile Ash | 8 | vs | 0 | New City Saints | 18 |
| 4186 | 07-Dec-2008 | R3 | Winner Match 13 | vs | Two Mile Ash | 19 | ||
| 4187 | 07-Dec-2008 | R3 | Scot Youth | vs | Halse United | 20 | ||
| 4188 | 07-Dec-2008 | R3 | Wolverton Tigermoths | vs | Willen Juniors Warriors | 21 | ||
| 4189 | 07-Dec-2008 | R3 | Cranfield Colts | vs | MK Wanderers A | 22 | ||
| 4190 | 07-Dec-2008 | R3 | Newport Pagnell Town | vs | Stony Stratford Town | 23 | ||
| 4191 | 07-Dec-2008 | R3 | Milton Keynes City | vs | Winslow United Tigers | 24 | ||
| 4192 | 07-Dec-2008 | R3 | Brackley Town | vs | Southside United Scorpions | 25 | ||
| 4193 | 07-Dec-2008 | R3 | Southside United Strikers | vs | Emberton Athletic | 26 | ||
| 4194 | 25-Jan-2009 | R4 | Winner Match 24 | vs | Winner Match 19 | 27 | ||
| 4195 | 25-Jan-2009 | R4 | Winner Match 26 | vs | Winner Match 20 | 28 | ||
| 4196 | 25-Jan-2009 | R4 | Winner Match 21 | vs | Winner Match 22 | 29 | ||
| 4197 | 25-Jan-2009 | R4 | Winner Match 23 | vs | Winner Match 25 | 30 | ||
| 4198 | 29-Mar-2009 | SF | Winner Match 27 | vs | Winner Match 28 | 31 | ||
| 4199 | 29-Mar-2009 | SF | Winner Match 29 | vs | Winner Match 30 | 32 | ||
| 4200 | Final | Winner Match 31 | vs | Winner Match 32 | 33 | |||