Ukrainian Cup 2001/02, Second stage |
 | 09.08.2001 | | Mashynobudivnyk (Druzhkivka) | – | Oskil (Kupyansk) | | 1:2 (1:0) |
| Druzhkivka |
Ukrainian Cup 2001/02, Second stage |
| 26.07.2001 | | Oskil (Kupyansk) | – | Mashynobudivnyk (Druzhkivka) | | 0:2 (0:1) |
| Kupyansk Oskol Stadium |
Ukrainian Cup 2001/02, First stage |
| 14.07.2001 | | Avanhard (Rovenky) | – | Oskil (Kupyansk) | | -:+ |
| |
Ukrainian Cup 2000/01, First stage. Second League Cup, 1/16 finals |
| 06.08.2000 | | Frunzrenets-Liha-99 (Sumy) | – | Oskil (Kupyansk) | | 2:1 (1:0) |
| Sumy |
Ukrainian Cup 1999/00, First stage. Second League Cup, 1/16 finals |
| 22.09.1999 | | Metalist-2 (Kharkiv) | – | Oskil (Kupyansk) | | 2:0 (1:0) |
| Kharkiv |
Ukrainian Cup 1999/00, First stage. Second League Cup, 1/16 finals |
| 01.09.1999 | | Oskil (Kupyansk) | – | Metalist-2 (Kharkiv) | | 0:1 (0:0) |
| Kupyansk Oskol Stadium |
Ukrainian Cup 1998/99, 1/128 finals |
| 29.08.1998 | | Zorya (Lugansk) | – | Oskil (Kupyansk) | | 2:0 (1:0) |
 | Lugansk |
Ukrainian Cup 1998/99, 1/128 finals |
| 25.08.1998 | | Oskil (Kupyansk) | – | Zorya (Lugansk) | | 0:0 |
| Kupyansk Oskol Stadium |
Ukrainian Cup 1997/98, 1/32 finals |
| 15.10.1997 | | Metalurh (Nikopol) | – | Oskil (Kupyansk) | | +:- |
| |
Ukrainian Cup 1997/98, 1/64 finals |
| 26.07.1997 | | Oskil (Kupyansk) | – | Shakhtar-2 (Donetsk) | | 2:1 (1:0) |
| Kupyansk Oskol Stadium |
Ukrainian Cup 1997/98, 1/64 finals |
| 22.07.1997 | | Shakhtar-2 (Donetsk) | – | Oskil (Kupyansk) | | 1:2 (0:0) |
| Makiivka |
Ukrainian Cup 1996/97, 1/16 finals |
| 09.10.1996 | | Oskil (Kupyansk) | – | Nyva (Vinnytsya) | | 2:3 (2:2) |
| Kupyansk Oskol Stadium |
Ukrainian Cup 1996/97, 1/32 finals |
| 18.09.1996 | | Oskil (Kupyansk) | – | Naftovyk (Okhtyrka) | | 0:0 aet,
pen. 3:2 |
| Kupyansk Spartak Stadium |
Ukrainian Cup 1996/97, 1/64 finals |
| 28.08.1996 | | Oskil (Kupyansk) | – | Metalist (Kharkiv) | | 1:0 (0:0) |
| Kupyansk Oskol Stadium |
Ukrainian Cup 1995/96, 1/32 finals |
| 19.10.1995 | | Metalurh (Novomoskovsk) | – | Oskil (Kupyansk) | | 1:0 (0:0) |
| Novomoskovsk |
Ukrainian Cup 1995/96, 1/64 finals |
| 16.10.1995 | | Oskil (Kupyansk) | – | Khimik (Severodonetsk) | | 2:0 (1:0) |
| Kupyansk Oskol Stadium |
Ukrainian Cup 1995/96, 1/128 finals |
| 01.08.1995 | | Dynamo (Slavyansk) | – | Oskil (Kupyansk) | | 0:1 aet
(0:0) |
| Sloviansk |
Ukrainian Cup 1994/95, 1/128 finals |
| 21.08.1994 | | Metalurh (Kryvyi Rih) | – | Oskil (Kupyansk) | | 1:0 (1:0) |
| Kryvyi Rih |
