Head to Head
| Elite Club Friendlies | 2015/08/05 16:15 | Tottenham v AC Milan | W | 2-0 |
Home History
| Elite Club Friendlies | 2018/07/29 03:00 | Barcelona v Tottenham | L | 7-5 |
| Elite Club Friendlies | 2018/07/26 02:00 | Roma v Tottenham | W | 1-4 |
| England Premier League | 2018/05/13 14:00 | Tottenham v Leicester | W | 5-4 |
| England Premier League | 2018/05/09 19:00 | Tottenham v Newcastle | W | 1-0 |
| England Premier League | 2018/05/05 14:00 | West Brom v Tottenham | L | 1-0 |
| England Premier League | 2018/04/30 19:00 | Tottenham v Watford | W | 2-0 |
| England FA Cup | 2018/04/21 16:15 | Man Utd v Tottenham | L | 2-1 |
| England Premier League | 2018/04/17 18:45 | Brighton v Tottenham | D | 1-1 |
Away History
| Elite Club Friendlies | 2018/07/26 03:00 | AC Milan v Man Utd | L | 9-10 |
| Elite Club Friendlies | 2018/07/20 15:00 | AC Milan v Novara | W | 2-0 |
| Italy Serie A | 2018/05/20 16:00 | AC Milan v Fiorentina | W | 5-1 |
| Italy Serie A | 2018/05/13 16:00 | Atalanta v AC Milan | D | 1-1 |
| Coppa Italia | 2018/05/09 19:00 | Juventus v AC Milan | L | 4-0 |
| Italy Serie A | 2018/05/05 16:00 | AC Milan v Verona | W | 4-1 |
| Italy Serie A | 2018/04/29 13:00 | Bologna v AC Milan | W | 1-2 |
| Italy Serie A | 2018/04/21 18:45 | AC Milan v Benevento | L | 0-1 |