 |
 |
| EURO Qualif. | 05/06/1999 | North Macedonia | - | Croatia | 1:1 | 5.000 |
| UI-Cup | 19/06/1999 | Cementarnica Skopje | - | Kolkheti-1913 Poti | 4:2 | 2.000 |
| UI-Cup | 03/07/1999 | Cementarnica Skopje | - | Rostselmash Rostov | 1:1 | 2.000 |
| CL QF | 28/07/1999 | FK Sloga Jugomagnat | - | Brøndby IF | 0:1 | 5.000 |
| EL QF | 12/08/1999 | Vardar Skopje | - | Legia Warszawa | 0:5 | ??? |
| EURO Qualif. | 08/09/1999 | North Macedonia | - | Yugoslavia | 2:4 | 18.000 |
| EURO Qualif. | 09/10/1999 | North Macedonia | - | Ireland | 1:1 | 4.500 |
North Macedonia