| April 2, 2016 |
Newcastle United FC Singapore Vs Chelsea FC Singapore |
6 - 4 |
| April 16, 2016 |
United 4 United FC Vs Chelsea FC Singapore |
Replayed |
| April 23, 2016 |
United 4 United FC Vs Chelsea FC Singapore |
9 - 0 |
| April 30, 2016 |
Gooners FC Vs Chelsea FC Singapore |
4 - 4 |
| May 7, 2016 |
SG Spurs Supporters Club Vs Chelsea FC Singapore |
1 - 3 |
| May 14, 2016 |
SG Everton Supporters Club Vs Chelsea FC Singapore |
0 - 7 |
| May 28, 2016 |
Chelsea FC Singapore Vs Gooners FC |
3 - 0 |
| June 4, 2016 |
Chelsea FC Singapore Vs Newcastle United FC Singapore |
1 - 5 |
| September 10, 2016 |
Chelsea FC Singapore Vs United 4 United FC |
|
