[3] FK Sileks 2-1 Vardar Skopje [5] 2021-08-29 14:00
Stadium: Gradski Stadion Kratovo Round: 2
Home Manager: Gorazd Mihajlov Away Manager: Nikola Ilievski
Head to Head
| North Macedonia First League | 2021/04/11 11:00 | FK Sileks v Vardar Skopje | W | 6-0 |
| North Macedonia First League | 2020/12/02 12:00 | FK Sileks v Vardar Skopje | W | 1-0 |
| North Macedonia First League | 2020/08/23 15:00 | Vardar Skopje v FK Sileks | W | 0-4 |
| North Macedonia First League | 2019/11/27 12:00 | FK Sileks v Vardar Skopje | D | 2-2 |
| North Macedonia First League | 2019/09/22 13:30 | Vardar Skopje v FK Sileks | L | 3-0 |
| North Macedonia First League | 2019/05/12 14:30 | FK Sileks v Vardar Skopje | W | 1-0 |
| North Macedonia First League | 2019/03/31 13:30 | Vardar Skopje v FK Sileks | L | 1-0 |
| North Macedonia First League | 2018/11/25 12:00 | FK Sileks v Vardar Skopje | L | 0-1 |
Home History
| North Macedonia Second League | 2021/08/25 14:00 | FK Kadino v FK Sileks | W | 0-3 |
| UEFA Conference League Qualifying | 2021/07/15 17:00 | CS Petrocub v FK Sileks | L | 1-0 |
| UEFA Conference League Qualifying | 2021/07/08 14:00 | FK Sileks v CS Petrocub | D | 1-1 |
| Europe Friendlies | 2021/06/28 15:30 | FK Sileks v Laci | W | 1-0 |
| Europe Friendlies | 2021/06/24 14:45 | FK Sileks v Teuta Durres | L | 0-1 |
| North Macedonia Play-Offs | 2021/05/25 14:00 | Tikves Kavadarci v FK Sileks | L | 1-0 |
| North Macedonia Cup | 2021/05/19 17:00 | AP Brera Strumica v FK Sileks | W | 3-4 |
| North Macedonia First League | 2021/05/16 14:00 | FK Sileks v FC Struga Trim & Lum | L | 0-1 |
Away History
| North Macedonia Second League | 2021/08/25 14:00 | FK Korabi v Vardar Skopje | D | 0-0 |
| Europe Friendlies | 2021/08/21 15:30 | Belasica Strumica v Vardar Skopje | W | 1-2 |
| Europe Friendlies | 2021/08/01 15:30 | Vardar Skopje v FK Pobeda | D | 1-1 |
| Europe Friendlies | 2021/07/28 08:00 | Vardar Skopje v Renova Dzepciste | D | 2-2 |
| Europe Friendlies | 2021/07/21 15:00 | FK Sasa v Vardar Skopje | D | 0-0 |
| North Macedonia First League | 2021/05/16 14:00 | Vardar Skopje v Makedonija Gj. P | L | 0-2 |
| North Macedonia First League | 2021/05/09 14:00 | FC Struga Trim & Lum v Vardar Skopje | L | 1-0 |
| North Macedonia First League | 2021/05/01 11:00 | Vardar Skopje v Rabotnicki Skopje | L | 1-3 |