Home History
| Barbados Super Cup | 2019/10/19 22:00 | Ellerton FC v Pride of Gall Hill FC | L | 2-0 |
| Barbados Super Cup | 2019/10/06 23:59 | Pride of Gall Hill FC v UWI Blackbirds | W | 1-0 |
| Barbados Super Cup | 2019/09/18 00:59 | Porey Springs v Pride of Gall Hill FC | D | 1-1 |
| Barbados Challenge Cup | 2017/06/11 00:37 | Pride of Gall Hill FC v Weymouth Wales | L | 0-3 |
Away History
| Barbados Super Cup | 2019/10/01 23:10 | Fitts Village v Youth Milan | W | 2-3 |
| Barbados Super Cup | 2019/09/24 22:59 | Paradise SC v Youth Milan | L | 4-3 |
| Barbados Super Cup | 2019/09/15 22:00 | Youth Milan v Wotton FC | W | 4-1 |
| Barbados Premier League | 2019/05/02 23:04 | Weymouth Wales v Youth Milan | L | 10-0 |
| Barbados Premier League | 2019/04/23 23:00 | Youth Milan v Barbados Soccer Academy | L | 1-2 |
| Barbados Premier League | 2019/04/07 01:00 | Porey Springs v Youth Milan | L | 6-0 |
| Barbados Premier League | 2019/03/30 23:00 | Notre Dame v Youth Milan | L | 5-1 |
| Barbados Premier League | 2019/03/16 21:02 | Paradise SC v Youth Milan | L | 10-0 |