| Liga | Tiempo(Mexico City) | Redondo | Equipos | Resultados | Puntaje |
| Friendlies Clubs | 06/14/22 09:00 | Club Friendlies 4 | Shkupi 1927 vs Ballkani | L | 0:2 |
| Friendlies Clubs | 06/19/22 07:00 | Club Friendlies 4 | Shkupi 1927 vs Tirana | L | 0:2 |
| Friendlies Clubs | 06/22/22 09:00 | Club Friendlies 2 | Fenerbahce vs Shkupi 1927 | D | 2:2 |
| Friendlies Clubs | 06/25/22 08:30 | Club Friendlies 3 | AFC Hermannstadt vs Shkupi 1927 | L | 2:0 |
| UEFA Champions League | 07/05/22 12:45 | 1st Qualifying Round | Shkupi 1927 vs Lincoln Red Imps FC | W | 3:0 |
| UEFA Champions League | 07/12/22 10:00 | 1st Qualifying Round | Lincoln Red Imps FC vs Shkupi 1927 | L | 2:0 |
| UEFA Champions League | 07/19/22 13:00 | 2nd Qualifying Round | Dinamo Zagreb vs Shkupi 1927 | D | 2:2 |
| UEFA Champions League | 07/26/22 13:00 | 2nd Qualifying Round | Shkupi 1927 vs Dinamo Zagreb | L | 0:1 |
| UEFA Europa League | 08/04/22 13:00 | 3rd Qualifying Round | Shamrock Rovers vs Shkupi 1927 | L | 3:1 |
| UEFA Europa League | 08/09/22 13:00 | 3rd Qualifying Round | Shkupi 1927 vs Shamrock Rovers | L | 1:2 |
| First League | 08/13/22 09:00 | Regular Season - 2 | Shkupi 1927 vs Makedonija GjP | W | 2:1 |
| UEFA Europa Conference League | 08/18/22 13:00 | Play-offs | Shkupi 1927 vs Ballkani | L | 1:2 |
| UEFA Europa Conference League | 08/25/22 12:00 | Play-offs | Ballkani vs Shkupi 1927 | L | 1:0 |
| First League | 08/28/22 08:00 | Regular Season - 4 | Skopje vs Shkupi 1927 | W | 0:2 |
| First League | 08/31/22 08:00 | Regular Season - 5 | Shkupi 1927 vs Pobeda | D | 1:1 |
| First League | 09/04/22 08:00 | Regular Season - 6 | Bregalnica Štip vs Shkupi 1927 | L | 2:0 |
| First League | 09/07/22 08:00 | Regular Season - 1 | Tikveš vs Shkupi 1927 | L | 3:1 |
| First League | 09/11/22 08:00 | Regular Season - 7 | Shkupi 1927 vs FK Rabotnicki | W | 5:0 |
| Cup | 09/14/22 07:00 | 1st Round | Belasica vs Shkupi 1927 | W | 1:3 |
| First League | 09/17/22 07:00 | Regular Season - 8 | Shkendija vs Shkupi 1927 | D | 0:0 |
| First League | 10/02/22 07:00 | Regular Season - 9 | Shkupi 1927 vs Sileks | D | 0:0 |
| Cup | 10/05/22 06:00 | Round of 16 | Shkupi 1927 vs Voska Sport | W | 6:0 |
| First League | 10/09/22 06:00 | Regular Season - 10 | Akademija Pandev vs Shkupi 1927 | W | 0:1 |
| First League | 10/16/22 06:00 | Regular Season - 11 | Shkupi 1927 vs Struga | W | 1:0 |
| First League | 10/26/22 06:00 | Regular Season - 12 | Shkupi 1927 vs Tikveš | W | 4:2 |
| First League | 10/30/22 06:00 | Regular Season - 13 | Makedonija GjP vs Shkupi 1927 | D | 1:1 |
| Cup | 11/09/22 06:00 | Quarter-finals | Shkupi 1927 vs Shkendija | L | 0:3 |
| First League | 11/12/22 06:00 | Regular Season - 15 | Shkupi 1927 vs Skopje | W | 3:1 |
| First League | 11/27/22 06:00 | Regular Season - 16 | Pobeda vs Shkupi 1927 | W | 0:6 |
| First League | 12/04/22 06:00 | Regular Season - 17 | Shkupi 1927 vs Bregalnica Štip | W | 3:1 |
| First League | 12/11/22 06:00 | Regular Season - 18 | FK Rabotnicki vs Shkupi 1927 | W | 2:4 |
| Friendlies Clubs | 01/15/23 18:00 | Club Friendlies 4 | Shkupi 1927 vs Pobeda | W | 4:2 |
| Friendlies Clubs | 01/30/23 18:00 | Club Friendlies 3 | Oleksandria vs Shkupi 1927 | W | 1:2 |
| Friendlies Clubs | 01/31/23 08:00 | Club Friendlies 5 | Shkupi 1927 vs Oleksandria | W | 2:1 |
| Friendlies Clubs | 02/08/23 08:00 | Club Friendlies 5 | Shkupi 1927 vs Pakhtakor | L | 1:4 |
| Friendlies Clubs | 02/11/23 06:00 | Club Friendlies 3 | FK Zalgiris Vilnius vs Shkupi 1927 | W | 0:4 |
| First League | 02/19/23 07:00 | Regular Season - 19 | Shkupi 1927 vs Shkendija | W | 2:0 |
| First League | 02/26/23 07:00 | Regular Season - 20 | Sileks vs Shkupi 1927 | L | 2:1 |
| First League | 03/04/23 07:00 | Regular Season - 21 | Shkupi 1927 vs Akademija Pandev | D | 3:3 |
| First League | 03/08/23 07:00 | Regular Season - 22 | Struga vs Shkupi 1927 | L | 2:1 |
| First League | 03/12/23 07:00 | Regular Season - 23 | Shkupi 1927 vs FK Rabotnicki | W | 3:1 |
| First League | 03/18/23 08:00 | Regular Season - 24 | Akademija Pandev vs Shkupi 1927 | D | 1:1 |
| Friendlies Clubs | 03/25/23 07:30 | Club Friendlies 5 | Lok. Skopje vs Shkupi 1927 | W | 1:2 |
| First League | 04/02/23 07:00 | Regular Season - 25 | Shkupi 1927 vs Skopje | L | 0:1 |
| First League | 04/09/23 07:00 | Regular Season - 26 | Pobeda vs Shkupi 1927 | W | 0:6 |
| First League | 04/23/23 08:00 | Regular Season - 28 | Tikveš vs Shkupi 1927 | D | 0:0 |
| First League | 04/26/23 08:00 | Regular Season - 29 | Shkupi 1927 vs Bregalnica Štip | W | 3:0 |
| First League | 04/30/23 08:00 | Regular Season - 30 | Sileks vs Shkupi 1927 | W | 0:2 |
| First League | 05/07/23 09:00 | Regular Season - 31 | Shkupi 1927 vs Shkendija | W | 2:1 |
| First League | 05/10/23 09:00 | Regular Season - 32 | Shkupi 1927 vs Makedonija GjP | W | 3:0 |
| First League | 05/14/23 09:00 | Regular Season - 33 | Struga vs Shkupi 1927 | L | 2:1 |
| Friendlies Clubs | 06/22/23 14:00 | Club Friendlies 5 | Shkupi 1927 vs AFC Hermannstadt | W | 2:1 |
| Friendlies Clubs | 06/26/23 08:00 | Club Friendlies 5 | Shkupi 1927 vs Egnatia Rrogozhinë | D | 1:1 |
| Friendlies Clubs | 07/06/23 09:30 | Club Friendlies 5 | Makedonija GjP vs Shkupi 1927 | W | 0:3 |
| UEFA Europa Conference League | 07/13/23 11:00 | 1st Qualifying Round | Hegelmann Litauen vs Shkupi 1927 | W | 0:5 |
| UEFA Europa Conference League | 07/20/23 13:00 | 1st Qualifying Round | Shkupi 1927 vs Hegelmann Litauen | D | 0:0 |
| UEFA Europa Conference League | 07/27/23 13:00 | 2nd Qualifying Round | Shkupi 1927 vs Levski Sofia | L | 0:2 |
| UEFA Europa Conference League | 08/03/23 11:00 | 2nd Qualifying Round | Levski Sofia vs Shkupi 1927 | L | 1:0 |
| First League | 08/07/23 09:00 | Regular Season - 1 | FK Rabotnicki vs Shkupi 1927 | L | 3:1 |
| First League | 08/13/23 09:00 | Regular Season - 2 | Vardar Skopje vs Shkupi 1927 | W | 0:1 |
| First League | 08/20/23 09:00 | Regular Season - 3 | Shkupi 1927 vs Sileks | D | 1:1 |
| First League | 08/23/23 08:30 | Regular Season - 4 | Makedonija GjP vs Shkupi 1927 | D | 0:0 |
| First League | 08/27/23 08:00 | Regular Season - 5 | Shkupi 1927 vs KF Gostivari | W | 3:1 |
