| Date | Time | Round | Home Team | Away Team | Venue | Referee | Score | |
| 07/09/2008 | 10.30 am | 1 | Brambles Farm FC | Lakes Utd B | Brambles Farm FC | M.Diccico | 2-3 | MR |
| 07/09/2008 | 10.30 am | 1 | Total Windows FC | Village Park Rangers | Prissick Base | R.Brine | 0-4 | MR |
| 07/09/2008 | 10.30 am | 1 | Roseberry Park FC | South Bank Minors | Mill Hill | | 0-19 | MR |
| 07/09/2008 | 10.30 am | 1 | Park End | Marton Taxis | Acorn Centre,Acklam | D.Holmes | 8-0 | MR |
| 07/09/2008 | 10.30 am | 1 | Acklam Electrical | Bulkhaul | Mill Hill | Mill Hill | 1-5 | MR |
| 07/09/2008 | 10.30 am | 1 | Stockton FC | Fatso's | Grangefield School | L.Parnaby | 0-3 | MR |
| 07/09/2008 | 10.30 am | 1 | Trader Jacks Marton Rovers | Linthorpe FC | Pallister Park | K.Bates | 4-0 | MR |
| 07/09/2008 | 10.30 am | 1 | Riverside | Courtyard | Newlands School, Saltersgill | S.Davison | 2-0 | MR |
| 07/09/2008 | 10.30 | 1 | Ormesby FC | D Campbell Tyres | Eston Academy? | R.Clark | pp | MR |
| 07/09/2008 | 10.30 am | 1 | Neon Nites | Beckfields FC | Prissick Base | P.Simpson | 1-5 | MR |
| 07/09/2008 | 10.30 am | 1 | The Pov | Lakes Utd | Tees Dock Park | A.Tonge | 6-2 | MR |
| 21/09/2008 | 10.30 am | 1 | Cleveland Cable | Iceland Teesside | Brambles Farm | M.Dicico | 5-3 | MR |
| 05/10/2008 | | 1 | Ormesby FC | D Campbell Tyres | Eston Academy | D.Holmes | 3-3 xtra time DC Tyres won on penalties 4-2 | MR |