| 29/05/2026 |   Septemvri Simitli vs Kyustendil | 2 - 0 | Third League - Southwest
Phase : J34 | 2025 | National Stadium Vasil Levski |
| 23/05/2026 |  Kyustendil vs Slivnishki geroy | 0 - 0 | Third League - Southwest
Phase : J33 | 2025 | - |
| 17/05/2026 |  Slavia Sofia II vs Kyustendil | 8 - 1 | Third League - Southwest
Phase : J32 | 2025 | - |
| 09/05/2026 |  Kyustendil vs Oborishte | 2 - 1 | Third League - Southwest
Phase : J31 | 2025 | - |
| 02/05/2026 |  Kyustendil vs Septemvri Sofia II | 0 - 0 | Third League - Southwest
Phase : J30 | 2025 | - |
| 25/04/2026 |  Kostinbrod vs Kyustendil | 2 - 1 | Third League - Southwest
Phase : J29 | 2025 | - |
| 09/04/2026 |  Rilski Sportist vs Kyustendil | 1 - 0 | Third League - Southwest
Phase : J27 | 2025 | - |
| 04/04/2026 |  Kyustendil vs Balkan Botevgrad | 0 - 0 | Third League - Southwest
Phase : J26 | 2025 | - |
| 28/03/2026 |  Strumska Slava vs Kyustendil | 3 - 1 | Third League - Southwest
Phase : J25 | 2025 | Stade Hristo Radovanov |
| 21/03/2026 |  Kyustendil vs Germaneya | 0 - 0 | Third League - Southwest
Phase : J24 | 2025 | - |
| 14/03/2026 |  Pirin Razlog vs Kyustendil | 1 - 2 | Third League - Southwest
Phase : J23 | 2025 | - |
| 07/03/2026 |  Kyustendil vs Bansko | 2 - 0 | Third League - Southwest
Phase : J22 | 2025 | - |
| 28/02/2026 |  Pirin Gotse Delchev vs Kyustendil | 2 - 1 | Third League - Southwest
Phase : J21 | 2025 | - |
| 21/02/2026 |  Kyustendil vs Botev Ihtiman | 0 - 2 | Third League - Southwest
Phase : J20 | 2025 | - |
| 04/02/2026 |  Vihren vs Kyustendil | 4 - 0 | Friendlies Clubs
Phase : Club Friendly | 2026 | - |
| 29/11/2025 |  CSKA Sofia III vs Kyustendil | 2 - 3 | Third League - Southwest
Phase : J19 | 2025 | National Stadium Vasil Levski |
| 22/11/2025 |  Kyustendil vs Levski Sofia II | 3 - 1 | Third League - Southwest
Phase : J18 | 2025 | Stadion Osogovo |
| 15/11/2025 | Kyustendil vs Septemvri Simitli | 1 - 0 | Third League - Southwest
Phase : J17 | 2025 | Stadion Osogovo |
| 08/11/2025 | Slivnishki geroy vs Kyustendil | 2 - 4 | Third League - Southwest
Phase : J16 | 2025 | Gradski stadion |
| 02/11/2025 | Kyustendil vs Slavia Sofia II | 4 - 3 | Third League - Southwest
Phase : J15 | 2025 | Stadion Osogovo |
| 25/10/2025 | Oborishte vs Kyustendil | 1 - 0 | Third League - Southwest
Phase : J14 | 2025 | Stadio Orcho voyvoda |
| 18/10/2025 | Septemvri Sofia II vs Kyustendil | 0 - 0 | Third League - Southwest
Phase : J13 | 2025 | Stadion German |
| 11/10/2025 | Kyustendil vs Kostinbrod | 0 - 2 | Third League - Southwest
Phase : J12 | 2025 | Stadion Osogovo |
| 04/10/2025 |  Vitosha Bistritsa vs Kyustendil | 2 - 1 | Third League - Southwest
Phase : J11 | 2025 | Stade Bistritsa |
| 27/09/2025 | Kyustendil vs Rilski Sportist | 1 - 2 | Third League - Southwest
Phase : J10 | 2025 | Stadion Osogovo |
| 20/09/2025 | Balkan Botevgrad vs Kyustendil | 3 - 1 | Third League - Southwest
Phase : J9 | 2025 | Stadion Hristo Botev |
| 17/09/2025 | Kyustendil vs Strumska Slava | 3 - 0 | Third League - Southwest
Phase : J8 | 2025 | Stadion Osogovo |
| 13/09/2025 | Germaneya vs Kyustendil | 1 - 2 | Third League - Southwest
Phase : J7 | 2025 | Gradski stadion |
| 06/09/2025 | Kyustendil vs Pirin Razlog | 1 - 0 | Third League - Southwest
Phase : J6 | 2025 | Stadion Osogovo |
| 30/08/2025 | Bansko vs Kyustendil | 2 - 3 | Third League - Southwest
Phase : J5 | 2025 | Stadion Sveti Petar |
| 23/08/2025 | Kyustendil vs Pirin Gotse Delchev | 2 - 1 | Third League - Southwest
Phase : J4 | 2025 | Stadion Osogovo |
| 16/08/2025 | Botev Ihtiman vs Kyustendil | 3 - 1 | Third League - Southwest
Phase : J3 | 2025 | Gradski stadion |
| 09/08/2025 | Kyustendil vs CSKA Sofia III | 5 - 3 | Third League - Southwest
Phase : J2 | 2025 | Stadion Osogovo |
| 02/08/2025 | Levski Sofia II vs Kyustendil | 2 - 1 | Third League - Southwest
Phase : J1 | 2025 | Georgi Asparuhov pomoshtno igrishte |
| 04/06/2025 | Septemvri Simitli vs Kyustendil | 3 - 1 | Third League - Southwest
Phase : J38 | 2024 | Stadion Struma |
| 31/05/2025 | Kyustendil vs CSKA Sofia III | 5 - 1 | Third League - Southwest
Phase : J37 | 2024 | Stadion Osogovo |
| 24/05/2025 | Slavia Sofia II vs Kyustendil | 2 - 4 | Third League - Southwest
Phase : J36 | 2024 | Slavija pomoshten teren |
| 17/05/2025 | Kyustendil vs Pirin Razlog | 6 - 0 | Third League - Southwest
Phase : J35 | 2024 | Stadion Osogovo |
| 14/05/2025 | Slivnishki geroy vs Kyustendil | 2 - 2 | Third League - Southwest
Phase : J34 | 2024 | Gradski stadion |
| 10/05/2025 | Kyustendil vs Bansko | 3 - 2 | Third League - Southwest
Phase : J33 | 2024 | Stadion Osogovo |
| 03/05/2025 | Vihren vs Kyustendil | 2 - 0 | Third League - Southwest
Phase : J32 | 2024 | Stadion Spartak |
| 26/04/2025 | Kyustendil vs Pirin Gotse Delchev | 4 - 1 | Third League - Southwest
Phase : J31 | 2024 | Stadion Osogovo |
| 23/04/2025 | Oborishte vs Kyustendil | 2 - 1 | Third League - Southwest
Phase : J30 | 2024 | Stadio Orcho voyvoda |
| 05/04/2025 | Kyustendil vs Botev Ihtiman | 4 - 1 | Third League - Southwest
Phase : J28 | 2024 | Stadion Osogovo |
| 02/04/2025 |  Granit Vladaya vs Kyustendil | 0 - 3 | Third League - Southwest
Phase : J27 | 2024 | Stadion Vladaia |
| 29/03/2025 |  Kyustendil vs CSKA 1948 Sofia III | 5 - 2 | Third League - Southwest
Phase : J26 | 2024 | Stadion Osogovo |
| 22/03/2025 | Rilski Sportist vs Kyustendil | 3 - 3 | Third League - Southwest
Phase : J25 | 2024 | Stadion Iskar |
| 15/03/2025 | Kyustendil vs Vitosha Bistritsa | 2 - 0 | Third League - Southwest
Phase : J24 | 2024 | Stadion Osogovo |
| 12/03/2025 | Balkan Botevgrad vs Kyustendil | 2 - 0 | Third League - Southwest
Phase : J23 | 2024 | Stadion Hristo Botev |
| 08/03/2025 | Kyustendil vs Septemvri Sofia II | 1 - 1 | Third League - Southwest
Phase : J22 | 2024 | Stadion Osogovo |
