| April 3, 2016 |
Winchester FC Vs Shield FC |
2 - 0 |
| April 10, 2016 |
Winchester FC Vs CF Amigos |
3 - 4 |
| April 17, 2016 |
Acolytes FC Vs Winchester FC |
2 - 5 |
| April 24, 2016 |
INazuma FC Vs Winchester FC |
7 - 2 |
| May 1, 2016 |
Winchester FC Vs Beepeelona FC |
2 - 6 |
| May 8, 2016 |
Winchester FC Vs Melwood FC SG |
Replayed |
| May 15, 2016 |
Shield FC Vs Winchester FC |
2 - 2 |
| May 22, 2016 |
CF Amigos Vs Winchester FC |
3 - 2 |
| May 29, 2016 |
Winchester FC Vs INazuma FC |
2 - 3 |
| June 5, 2016 |
Winchester FC Vs Acolytes FC |
0 - 0 |
| July 10, 2016 |
Winchester FC Vs Melwood FC SG |
1 - 3 |
| July 24, 2016 |
Melwood FC SG Vs Winchester FC |
|
