| 09/07/08 |
| Mantua 1 Winslow 4 |
| Goalscorers: |
| Jerry Engle(2) |
| Filippo Cammarata |
| Bill MacDonald |
| |
| 09/14/08 |
| Winslow 5 Laurel Springs 1 |
| Goalscorers: |
| Ani Miramontes |
| Jerry Engle |
| Jimmy Turner |
| Dave Beahon |
| Billy Heins |
| |
| 09/21/08 |
| Mount Holly 0 Winslow 2 |
| Goalscorers: |
| Andy Tonia |
| Jimmy Turner |
| |
| 09/28/08 |
| Harrison 0 Winslow 5 |
| Goalscorers: |
| Filippo Cammarata(2) |
| Andy Tonia |
| Paul Alford |
| Bill MacDonald |
| |
| 10/05/08 |
| Winslow 2 Northern Burlington 2 |
| Goalscorers: |
| Andy Tonia |
| Dave Beahon |
| |
| 10/12/08 |
| Gibbsboro2 1 Winslow 0 |
| |
| 10/19/08 |
| Winslow 2 Moorestown2 1 |
| Goalscorers: |
| Andy Tonia |
| Jerry Engle |
| |
| 10/26/08 |
| Winslow 4 Gibbsboro2 0 |
| Goalscorers: |
| Andy Tonia |
| Own goal |
| Filippo Cammarata |
| Giuseppe Rizzo |
| |
| 11/02/08 |
| Winslow 2 Mount Holly 2 |
| Goalscorers: |
| Jay Peterson |
| Own goal |
| |
| 11/09/08 |
| Laurel Springs 1 Winslow 3 |
| Goalscorers: |
| Giuseppe Rizzo |
| Billy Heins |
| Jimmy Turner |
|
| 11/16/08 |
| Winslow at Mantua |
| Rained out |
|
| 11/23/08 |
| Moorestown2 3 Winslow 0 |
| |
| 11/30/08 |
| Winslow 4 Deptford 2 |
| Goalscorers: |
| Jerry Engle(2) |
| Jay Peterson |
| Jimmy Turner |
| |
| 12/07/08 |
| Northern Burlington 1 Winslow 4 |
Goalscorers: |
| Bill MacDonald(2) |
| Graham Hollywood |
| Giuseppe Rizzo |
| |
