Head to Head
| UEFA Champions League | 2023/02/14 20:00 | AC Milan v Tottenham | L | 1-0 |
| Elite Club Friendlies | 2018/08/01 00:30 | Tottenham v AC Milan | W | 1-0 |
| Elite Club Friendlies | 2015/08/05 16:15 | Tottenham v AC Milan | W | 2-0 |
Home History
| England Premier League | 2023/03/04 15:00 | Wolverhampton v Tottenham | L | 1-0 |
| England FA Cup | 2023/03/01 19:55 | Sheff Utd v Tottenham | L | 1-0 |
| England Premier League | 2023/02/26 13:30 | Tottenham v Chelsea | W | 2-0 |
| England Premier League | 2023/02/19 16:30 | Tottenham v West Ham | W | 2-0 |
| UEFA Champions League | 2023/02/14 20:00 | AC Milan v Tottenham | L | 1-0 |
| 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 |
Away History
| Italy Serie A | 2023/03/04 19:45 | Fiorentina v AC Milan | L | 2-1 |
| Italy Serie A | 2023/02/26 19:45 | AC Milan v Atalanta | W | 2-0 |
| Italy Serie A | 2023/02/18 17:00 | Monza v AC Milan | W | 0-1 |
| UEFA Champions League | 2023/02/14 20:00 | AC Milan v Tottenham | W | 1-0 |
| 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 |