| Bulgaria U19 League | 2019/08/22 15:00 | Montana 1921 U19 v Tsarsko Selo Sofia U19 | W | 0-3 |
| Bulgaria U19 League | 2020/02/21 11:30 | Tsarsko Selo Sofia U19 v Beroe Stara Zagora U19 | L | 0-1 |
| Bulgaria U19 League | 2019/10/30 12:30 | Tsarsko Selo Sofia U19 v Yantra Gabrovo U19 | L | 3-5 |
| Bulgaria U19 League | 2019/10/18 12:30 | Tsarsko Selo Sofia U19 v Levski Sofia U19 | L | 2-3 |
| Bulgaria U19 League | 2019/10/03 13:00 | FK Vereya Stara Zagora U19 v Tsarsko Selo Sofia U19 | D | 1-1 |
| Bulgaria U19 League | 2019/08/29 15:00 | Tsarsko Selo Sofia U19 v Ludogorets Razgrad U19 | L | 1-3 |
| Bulgaria U19 League | 2019/08/22 15:00 | Montana 1921 U19 v Tsarsko Selo Sofia U19 | W | 0-3 |
| Bulgaria U19 League | 2019/08/14 15:00 | Tsarsko Selo Sofia U19 v Septemvri Sofia U19 | W | 2-1 |
| Bulgaria U19 League | 2019/12/08 11:30 | Botev Plovdiv U19 v Montana 1921 U19 | L | 1-0 |
| Bulgaria U19 League | 2019/10/24 08:00 | Dunav Ruse U19 v Montana 1921 U19 | D | 2-2 |
| Bulgaria U19 League | 2019/10/18 12:30 | Montana 1921 U19 v CSKA Sofia U19 | L | 0-1 |
| Bulgaria U19 League | 2019/10/03 13:00 | Pirin Blagoevgrad U19 v Montana 1921 U19 | L | 5-0 |
| 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 |