| Date | Opponents | Venue | HT | Result | Scorers | M-o-M |
| 07/09/08 | Cliffe Woods Colts | Cliffe Rec | 1-1 | 2 - 4 | Speller, Turnham | Jarrett |
| 21/08/08 | Stirling 2000 | Woodstock | 0-0 | 1 - 2 | Speller | Watson |
| 26/10/08 | Medway 2000 | Snodhurst | 1-1 | 3 - 5 | Speller2, Barry | Turnham |
| 09/11/08 | Stockbury Athletic | MSC | 3-0 | 5 - 2 | Speller2, Hussey, Delport, Rothery | Parker |
| 16/11/08 | Sportsman | Woodstock | 1-1 | 5 - 2 | Baverstock3, Speller, Hussey | Baverstock |
| 23/11/08 | Stirling 2000 | Rainham Rec | 1-1 | 1 - 3 | Speller | tba |
| 30/11/08 | Sportsman | Knights Place | 1-1 | 4 - 4 | Baverstock2*, Hussey, Harris | Parker |
| 21/12/08 | Inter Gills | Woodstock | 0-0 | 1 - 1 | Speller | Jarrett |
| 04/01/09 | Elite '05 | Knights Place | 0-0 | 0 - 1 | - | J.Oswell |
| 11/01/09 | Horsted | Woodstock | PP | |||
| 18/01/09 | Inter Gills | Deangate | 2-0 | 3 - 2 | J.Oswell, Speller, Baverstock | Jarrett |
| 25/01/09 | Stockbury | Woodstock | PP | |||
| 01/02/09 | Cliffe Woods Colts | Woodstock | 0-0 | 2 - 2 | Speller, Baverstock | Parker |
| 08/02/09 | Medway 2000 | Woodstock | 5-0 | 9 - 0 | Speller4, J.Oswell2, Barry, Austin, Spillet | Speller |
| 01/03/09 | Scorpions Res | Woodstock | 1-3 | 3 - 3 | Speller2, Delport | Wildish |
| 15/03/09 | Pegasus | Woodstock | 2-3 | 2 - 7 | Speller2 | Austin |
| 22/03/09 | Elite '05 | Woodstock | 0-1 | 1 - 2 | J.Oswell | J.Oswell |
| 29/03/09 | Spartac Reserves | Woodstock | 3-0 | 4-1 | Delport2, Speller, Parker | Turnham |
| 29/03/09 | Spartac Reserves | Woodstock | 0-1 | 2 - 1 | Delport2 | Speller |
| TBA | Horsted | Home | ||||
| TBA | Pegasus | Away | ||||
| TBA | Horsted | Away | ||||
| TBA | Stockbury | Home | ||||
| TBA | Scorpions Res | Away |
| Date | Opponents | Venue | Competition | Halftime | Result | Scorers | M-o-M |
| 14/09/08 | Innbar Taverns | Knight's Place | Junior Cup | 0-3 | 1-11 | Speller | - |
| 28/09/08 | Lordswood Panthers | Woodstock | Kent Junior Trophy | 0-0 | 2-1 | Wildish, Speller * | Parker |
| 19/10/08 | Elite 05 | Woodstock | Kent Junior Trophy | 0-2 | 1-3 | Speller | Watson |
| 07/12/08 | Medway 2000 | Woodstock | Junior Charity Cup R1 | 3-0 | 6 - 3 aet | Speller2, Wildish2, Watson, Turnham | Watson |
| 15/02/09 | Stirling 2000 | Rainham Rec | Junior Charity Cup R2 | 3-0 | 5 - 0 | Speller2, Watson2, Baverstock | J.Oswell |
| 08/03/09 | Lordswood SC | Temple School | Junior Charity Cup QF | 2-0 | 2 - 1 | Speller, Parker | Turnham |
| 12/04/09 | Rainham '84 | Beechings Cross | Junior Charity Semi Final |
| Date | Opponents | Venue | Competition | Result | Scorers | M-o-M |
| 10/08/08 | Midas | UK Paper | Friendly | 5-4 | Hussey2, Turnham2*, Speller | Goodrum |
| 17/08/08 | Minster College | Minster College | Friendly | 7-5 | Speller3, J.Baverstock3, D.Baverstock | Speller |
| 24/08/08 | J.D.Decking | Sittingbourne | Friendly | 22-1 | J.Baverstock7, Speller5, L.Parker3, Hussey2, Wildish, Austin, Jarrett, Delport, o.g. | J.Baverstock |
| 31/08/08 | White Horse | Sittingbourne | Friendly | 0-7 | - | Watson |
* denotes penalty