Head to Head
| Euroleague | 2019/03/14 19:45 | Mailand v Olympiacos | W | 66-57 |
| Euroleague | 2018/10/19 18:00 | Olympiacos v Mailand | W | 75-99 |
| Euroleague | 2018/01/05 19:00 | Olympiacos v Mailand | L | 87-80 |
| Euroleague | 2017/11/23 19:45 | Mailand v Olympiacos | L | 85-86 |
| Euroleague | 2017/01/25 19:45 | Mailand v Olympiacos | W | 99-83 |
| Euroleague | 2016/10/25 18:00 | Olympiacos v Mailand | L | 91-81 |
| Euroleague | 2015/12/03 20:00 | Olympiacos v Mailand | L | 73-63 |
| Euroleague | 2015/10/30 19:45 | Mailand v Olympiacos | L | 66-71 |
Home History
| Freundschaftsspiele | 2019/09/01 18:14 | Mailand v Cantu | W | 66-54 |
| Freundschaftsspiele | 2019/08/31 16:00 | Mailand v Monferrato | W | 76-73 |
| Italien - Lega 1 | 2019/06/02 18:45 | Dinamo Sassari v Mailand | L | 108-96 |
| Italien - Lega 1 | 2019/05/31 18:45 | Mailand v Dinamo Sassari | L | 101-112 |
| Italien - Lega 1 | 2019/05/29 18:45 | Mailand v Dinamo Sassari | L | 79-86 |
| Italien - Lega 1 | 2019/05/26 18:30 | Mailand v Del Fes Avellino | W | 92-76 |
| Italien - Lega 1 | 2019/05/24 18:30 | Del Fes Avellino v Mailand | W | 80-86 |
| Italien - Lega 1 | 2019/05/22 18:30 | Del Fes Avellino v Mailand | L | 69-62 |
Away History
| Griechenland - A1 | 2019/05/08 14:30 | Olympiacos v Promitheas | W | 86-59 |
| Griechenland - A1 | 2019/05/04 14:30 | Olympiacos v Kolossos Rhodes | W | 95-74 |
| Griechenland - A1 | 2019/04/20 13:45 | AEK v Olympiacos | W | 67-76 |
| Griechenland - A1 | 2019/04/13 12:45 | Olympiacos v PAOK | W | 80-59 |
| Griechenland - A1 | 2019/04/10 15:00 | Peristeri v Olympiacos | L | 81-76 |
| Euroleague | 2019/04/05 18:30 | Olympiacos v Darussafaka | W | 99-74 |
| Griechenland - A1 | 2019/04/01 13:45 | Rethymno Cretan Kings v Olympiacos | W | 58-92 |
| Euroleague | 2019/03/29 19:30 | Olympiacos v Zalgiris | L | 68-72 |