[1] AC Milan 3-1 Olympiakos [2] 2018-10-04 16:55
Stadium: Giuseppe Meazza Round: 2
Referee: Robert Madden Home Manager: Gennaro Ivan Gattuso Away Manager: Pedro Rui Mota Vieira Martins
Home History
| Włochy - Serie A | 2018/09/30 18:30 | Sassuolo v AC Milan | W | 1-4 |
| Włochy - Serie A | 2018/09/27 19:00 | Empoli v AC Milan | D | 1-1 |
| Włochy - Serie A | 2018/09/23 16:00 | AC Milan v Atalanta | D | 2-2 |
| Liga Europy UEFA | 2018/09/20 19:00 | F91 Dudelange v AC Milan | W | 0-1 |
| Włochy - Serie A | 2018/09/16 18:30 | Cagliari v AC Milan | D | 1-1 |
| Włochy - Serie A | 2018/08/31 18:30 | AC Milan v Roma | W | 2-1 |
| Włochy - Serie A | 2018/08/25 18:30 | Napoli v AC Milan | L | 3-2 |
| Europa - Towarzyskie | 2018/08/11 19:00 | Real Madryt v AC Milan | L | 3-1 |
Away History
| Grecja - Super League 1 | 2018/09/30 17:30 | Olympiakos v PAOK Saloniki | L | 0-1 |
| Puchar Grecji | 2018/09/27 18:30 | Olympiakos v Levadiakos | W | 1-0 |
| Grecja - Super League 1 | 2018/09/24 16:30 | Panionios v Olympiakos | W | 0-1 |
| Liga Europy UEFA | 2018/09/20 19:00 | Olympiakos v Real Betis | D | 0-0 |
| Grecja - Super League 1 | 2018/09/16 17:30 | Olympiakos v Asteras Tripolis | W | 2-1 |
| Grecja - Super League 1 | 2018/09/02 18:30 | Olympiakos v Giannina | W | 5-0 |
| Liga Europy UEFA - Kwalifikacje | 2018/08/30 18:45 | Burnley v Olympiakos | D | 1-1 |
| Grecja - Super League 1 | 2018/08/26 18:30 | Olympiakos v Levadiakos | W | 1-0 |