Head to Head
| Euroleague | 2023/03/03 19:30 | Milano v Olympiacos | L | 83-62 |
| Euroleague | 2023/01/06 19:00 | Olympiacos v Milano | W | 82-66 |
| Euroleague | 2022/02/24 19:45 | Olympiacos v Milano | W | 67-58 |
| Euroleague | 2021/11/26 19:30 | Milano v Olympiacos | W | 72-93 |
| Euroleague | 2021/01/26 19:45 | Milano v Olympiacos | L | 90-79 |
| Euroleague | 2020/10/14 16:30 | Olympiacos v Milano | W | 86-75 |
| Euroleague | 2019/11/29 19:30 | Olympiacos v Milano | W | 91-70 |
| Club Friendlies | 2019/09/06 16:30 | Milano v Olympiacos | L | 78-62 |
Home History
| Club Friendlies | 2023/09/07 15:00 | Promitheas v Olympiacos | L | 61-45 |
| Greece A1 | 2023/06/15 18:15 | Panathinaikos v Olympiacos | W | 35-63 |
| Greece A1 | 2023/06/11 18:15 | Olympiacos v Panathinaikos | W | 75-52 |
| Greece A1 | 2023/06/08 18:15 | Panathinaikos v Olympiacos | L | 67-65 |
| Greece A1 | 2023/06/04 18:15 | Olympiacos v Panathinaikos | W | 73-70 |
| Greece A1 | 2023/05/28 16:05 | Olympiacos v PAOK | W | 75-54 |
| Greece A1 | 2023/05/25 16:15 | PAOK v Olympiacos | W | 77-97 |
| Euroleague | 2023/05/21 17:00 | Olympiacos v Real Madrid | L | 78-79 |
Away History
| Club Friendlies | 2023/09/10 18:22 | Dinamo Sassari v Milano | W | 63-83 |
| Club Friendlies | 2023/09/09 16:00 | Milano v Asvel Lyon-Villeurbanne | W | 95-78 |
| Club Friendlies | 2023/09/06 18:30 | Derthona Basket v Milano | W | 86-96 |
| Italy Lega 1 | 2023/06/23 18:30 | Milano v Virtus Bologna | W | 67-55 |
| Italy Lega 1 | 2023/06/21 18:30 | Virtus Bologna v Milano | L | 85-66 |
| Italy Lega 1 | 2023/06/19 18:30 | Milano v Virtus Bologna | W | 79-72 |
| Italy Lega 1 | 2023/06/16 18:30 | Virtus Bologna v Milano | L | 93-89 |
| Italy Lega 1 | 2023/06/14 18:30 | Virtus Bologna v Milano | L | 69-61 |