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The 1998–99 Macedonian Football Cup was the 7th season of Macedonia's football knockout competition. Vardar defended their title, having won their fourth title.
| Tournament details | |
|---|---|
| Country |  Macedonia |
| Dates | 2 August 1998 – 22 May 1999[1] |
| Teams | 32 |
| Defending champions | Vardar |
| Final positions | |
| Champions | Vardar (4th title) |
| Runner-up | Sloga Jugomagnat |
| Round | Date(s) | Fixtures | Clubs | New entries |
|---|---|---|---|---|
| First Round | 2 August 1998 | 16 | 32 → 16 | 32 |
| Group stage | 9, 23 September, 7 October, 11, 29 November 1998 & 28 February 1999 | 48 | 16 → 8 | none |
| Quarter-finals | 10, 17 March 1999 | 8 | 8 → 4 | none |
| Semi-finals | 7, 21 April 1999 | 4 | 4 → 2 | none |
| Final | 22 May 1999 | 1 | 2 → 1 | none |
Source:[1]
 |
The most results are unknown.
Group 1
Pobeda and Vardar were advanced to the quarterfinal, the other teams in group were Kumanovo and Sasa.
Group 2
![[icon]](#/media/File:Wiki_letter_w_cropped.svg){kind=small} | This section is empty. You can help by adding to it. (September 2022) |
Group 3
| This section is empty. You can help by adding to it. (September 2022) |
Group 4
Sileks and Osogovo were advanced to the quarterfinal, the other teams in group were Pelister and Ilinden Skopje.
The first legs were played on 10 March and second were played on 17 March 1999.
| Team 1 | Agg. | Team 2 | 1st leg | 2nd leg |
|---|---|---|---|---|
| Cementarnica | 2–3 | Vardar | 2–2 | 0–1 |
| Pobeda | 3–1 | Makedonija G.P. | 2–0 | 1–1 |
| Osogovo | 0–5 | Sloga Jugomagnat | 0–2 | 0–3 |
| Rabotnichki Kometal | 1–3 | Sileks | 1–0 | 0–3 |
The first legs were played on 7 April and the second were played on 21 April 1999.
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