Head to Head
| Euroleague | 2019/11/29 19:30 | Olympiacos v Milano | L | 91-70 |
| Club Friendlies | 2019/09/06 16:30 | Milano v Olympiacos | W | 78-62 |
| Euroleague | 2019/03/14 19:45 | Milano v Olympiacos | W | 66-57 |
| Euroleague | 2018/10/19 18:00 | Olympiacos v Milano | W | 75-99 |
| Euroleague | 2018/01/05 19:00 | Olympiacos v Milano | L | 87-80 |
| Euroleague | 2017/11/23 19:45 | Milano v Olympiacos | L | 85-86 |
| Euroleague | 2017/01/25 19:45 | Milano v Olympiacos | W | 99-83 |
| Euroleague | 2016/10/25 18:00 | Olympiacos v Milano | L | 91-81 |
| Euroleague | 2015/12/03 20:00 | Olympiacos v Milano | L | 73-63 |
| Euroleague | 2015/10/30 19:45 | Milano v Olympiacos | L | 66-71 |
| Euroleague | 2015/03/06 19:45 | Milano v Olympiacos | L | 74-83 |
| Euroleague | 2015/01/08 19:45 | Olympiacos v Milano | L | 81-58 |