Head to Head
| Elite Club Friendlies | 2018/08/01 00:30 | Tottenham v AC Milan | L | 1-0 |
| Elite Club Friendlies | 2015/08/05 16:15 | Tottenham v AC Milan | L | 2-0 |
Home History
| Italy Serie A | 2023/02/10 19:45 | AC Milan v Torino | W | 1-0 |
| Italy Serie A | 2023/02/05 19:45 | Inter Milan v AC Milan | L | 1-0 |
| Italy Serie A | 2023/01/29 11:30 | AC Milan v Sassuolo | L | 2-5 |
| Italy Serie A | 2023/01/24 19:45 | Lazio v AC Milan | L | 4-0 |
| Italy Super Cup | 2023/01/18 19:00 | AC Milan v Inter Milan | L | 0-3 |
| Italy Serie A | 2023/01/14 17:00 | Lecce v AC Milan | D | 2-2 |
| Coppa Italia | 2023/01/11 20:00 | AC Milan v Torino | D | 0-0 |
| Italy Serie A | 2023/01/08 19:45 | AC Milan v Roma | D | 2-2 |
Away History
| England Premier League | 2023/02/11 15:00 | Leicester v Tottenham | L | 4-1 |
| England Premier League | 2023/02/05 16:30 | Tottenham v Man City | W | 1-0 |
| England FA Cup | 2023/01/28 18:00 | Preston v Tottenham | W | 0-3 |
| England Premier League | 2023/01/23 20:15 | Fulham v Tottenham | W | 0-1 |
| England Premier League | 2023/01/19 20:00 | Man City v Tottenham | L | 4-2 |
| England Premier League | 2023/01/15 16:30 | Tottenham v Arsenal | L | 0-2 |
| England FA Cup | 2023/01/07 12:30 | Tottenham v Portsmouth | W | 1-0 |
| England Premier League | 2023/01/04 20:00 | Crystal Palace v Tottenham | W | 0-4 |