| Date | R | Home v Away | - | |
|---|---|---|---|---|
| 05/02 23:04 | - | Weymouth Wales v Youth Milan | L | 10-0 |
| 04/23 23:00 | - | Youth Milan v Barbados Soccer Academy | L | 1-2 |
| 04/07 01:00 | - | Porey Springs v Youth Milan | L | 6-0 |
| 03/30 23:00 | - | Notre Dame v Youth Milan | L | 5-1 |
| 03/16 21:02 | - | Paradise FC v Youth Milan | L | 10-0 |
| 03/09 22:55 | - | Youth Milan v Empire Club | L | 0-4 |
| 02/24 01:00 | - | St Andrew Lions v Youth Milan | L | 3-1 |
| 02/16 23:00 | - | Youth Milan v Ellerton FC | L | 1-4 |
| 02/10 01:01 | - | BDF Sport Programme v Youth Milan | L | 7-0 |
| 02/03 22:00 | - | Weymouth Wales v Youth Milan | L | 3-0 |
| 01/27 01:00 | - | Barbados Soccer Academy v Youth Milan | D | 1-1 |
| 01/19 23:02 | - | Youth Milan v Notre Dame | L | 0-1 |
| 01/12 22:59 | - | Youth Milan v Porey Springs | D | 2-2 |
| 12/17 00:00 | - | Youth Milan v UWI Blackbirds | L | 1-5 |
| 12/10 00:00 | - | Youth Milan v St Andrew Lions | W | 1-0 |
| 12/02 22:00 | - | Youth Milan v BDF Sport Programme | L | 0-1 |
| 11/28 01:00 | - | Ellerton FC v Youth Milan | W | 1-2 |
| 11/04 22:03 | - | Empire Club v Youth Milan | L | 2-0 |
| 10/23 22:58 | - | Youth Milan v Paradise FC | D | 1-1 |