| Elite Club Friendlies | 2019/08/03 16:30 | Man Utd v AC Milan | L | 7-6 |
| Elite Club Friendlies | 2019/07/28 19:00 | AC Milan v Benfica | L | 0-1 |
| Elite Club Friendlies | 2019/07/24 01:00 | Bayern Munich v AC Milan | L | 1-0 |
| Italy Serie A | 2019/05/26 18:30 | Spal v AC Milan | W | 2-3 |
| Italy Serie A | 2019/05/19 16:00 | AC Milan v Frosinone | W | 2-0 |
| Italy Serie A | 2019/05/11 18:30 | Fiorentina v AC Milan | W | 0-1 |
| Italy Serie A | 2019/05/06 18:30 | AC Milan v Bologna | W | 2-1 |
| Italy Serie A | 2019/04/28 18:30 | Torino v AC Milan | L | 2-0 |
| Europe Friendlies | 2019/07/27 18:00 | Lecce v Frosinone | W | 4-1 |
| Europe Friendlies | 2019/07/25 15:00 | Lecce v Virtus Bolzano | W | 6-0 |
| Italy Serie B | 2019/05/11 13:00 | Lecce v Spezia | W | 2-1 |
| Italy Serie B | 2019/05/01 13:00 | Padova v Lecce | L | 2-1 |
| Italy Serie B | 2019/04/28 19:00 | Lecce v Brescia | W | 1-0 |
| Italy Serie B | 2019/04/22 19:00 | Perugia v Lecce | W | 1-2 |
| Italy Serie B | 2019/04/13 13:00 | Lecce v AC Carpi | W | 4-1 |
| Italy Serie B | 2019/04/07 13:00 | Cremonese v Lecce | L | 2-0 |