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 |
Home History
| Euroleague | 2020/03/05 20:00 | Valencia v Milano | W | 81-83 |
| Euroleague | 2020/03/03 19:45 | Milano v Real Madrid | L | 73-78 |
| Euroleague | 2020/02/28 18:00 | Zalgiris v Milano | L | 105-97 |
| Euroleague | 2020/02/20 19:45 | Milano v Khimki Moscow Region | L | 69-78 |
| Coppa Italia | 2020/02/15 16:45 | Venezia v Milano | L | 67-63 |
| Coppa Italia | 2020/02/13 17:00 | Milano v Vanoli Cremona | W | 86-62 |
| Italy Lega 1 | 2020/02/09 16:00 | Milano v Vanoli Cremona | W | 77-74 |
| Euroleague | 2020/02/07 20:00 | Barcelona v Milano | L | 84-80 |
Away History
| Greece A2 | 2020/03/07 15:00 | Olympiacos v Apollon Patras | W | 98-68 |
| Euroleague | 2020/03/06 17:30 | Anadolu Efes v Olympiacos | L | 91-79 |
| Euroleague | 2020/03/03 19:00 | Olympiacos v Panathinaikos | W | 81-78 |
| Greece Elite League | 2020/02/29 15:00 | Amyntas v Olympiacos | W | 69-81 |
| Euroleague | 2020/02/27 19:05 | Maccabi Tel Aviv v Olympiacos | L | 71-70 |
| Greece A2 | 2020/02/22 15:00 | Olympiacos v Oiakas Nafpliou | W | 73-67 |
| Euroleague | 2020/02/20 17:15 | Olympiacos v Asvel Lyon-Villeurbanne | W | 77-68 |
| Greece A2 | 2020/02/15 15:00 | Filippos Veroias v Olympiacos | W | 70-85 |