| Bulgaria U19 League | 2019/05/03 13:30 | Montana 1921 U19 v Pirin Blagoevgrad U19 | L | 2-0 |
| Bulgaria U19 League | 2018/10/19 12:30 | Pirin Blagoevgrad U19 v Montana 1921 U19 | W | 2-1 |
| Bulgaria U19 League | 2019/08/30 15:00 | Marek Dupnitsa U19 v Pirin Blagoevgrad U19 | W | 0-2 |
| Bulgaria U19 League | 2019/08/23 15:00 | Pirin Blagoevgrad U19 v Yantra Gabrovo U19 | L | 0-2 |
| Bulgaria U19 League | 2019/08/14 15:00 | Botev Plovdiv U19 v Pirin Blagoevgrad U19 | L | 5-0 |
| Bulgaria U19 League | 2019/08/10 15:00 | Pirin Blagoevgrad U19 v Levski Sofia U19 | L | 0-4 |
| Bulgaria U19 League | 2019/05/29 15:00 | Pirin Blagoevgrad U19 v Neftochimic Burgas U19 | D | 1-1 |
| Bulgaria U19 League | 2019/05/18 15:00 | Pirin Blagoevgrad U19 v Cherno More Varna U19 | L | 1-4 |
| Bulgaria U19 League | 2019/05/13 13:30 | CSKA Sofia U19 v Pirin Blagoevgrad U19 | L | 1-0 |
| Bulgaria U19 League | 2019/05/03 13:30 | Montana 1921 U19 v Pirin Blagoevgrad U19 | L | 2-0 |
| Bulgaria U19 League | 2019/09/15 14:00 | Septemvri Sofia U19 v Montana 1921 U19 | L | 3-0 |
| Bulgaria U19 League | 2019/08/30 15:00 | Lokomotiv Plovdiv U19 v Montana 1921 U19 | L | 3-2 |
| Bulgaria U19 League | 2019/08/22 15:00 | Montana 1921 U19 v Tsarsko Selo Sofia U19 | L | 0-3 |
| Bulgaria U19 League | 2019/08/14 15:00 | Marek Dupnitsa U19 v Montana 1921 U19 | W | 1-2 |
| Bulgaria U19 League | 2019/05/29 15:00 | Montana 1921 U19 v Cherno More Varna U19 | W | 1-0 |
| Bulgaria U19 League | 2019/05/24 15:00 | Lokomotiv Plovdiv U19 v Montana 1921 U19 | D | 1-1 |
| Bulgaria U19 League | 2019/05/20 14:00 | Montana 1921 U19 v CSKA Sofia U19 | W | 1-0 |
| Bulgaria U19 League | 2019/05/13 13:30 | Marek Dupnitsa U19 v Montana 1921 U19 | L | 3-2 |