# 1999–2000 Macedonian Football Cup

The 1999–2000 Macedonian Football Cup was the 8th season of Macedonia's football knockout competition. Vardar were the defending champions, having won their fourth title. The 1999–2000 champions were Sloga Jugomagnat who won their second title.

## Competition calendar

| Round | Date(s) | Fixtures | Clubs | New entries |
| First Round | 15 September 1999 | 16 | 32 → 16 | 32 |
| Group stage | 22, 29 September, 20 October, 10, 28 November 1999 & 27 February 2000 | 48 | 16 → 8 | none |
| Quarter-finals | 15, 22 March 2000 | 8 | 8 → 4 | none |
| Semi-finals | 5, 19, 20 April 2000 | 4 | 4 → 2 | none |
| Final | 20 May 2000 | 1 | 2 → 1 | none |
Source:

## First round

| Team 1 | Score | Team 2 |
| Shkëndija HB | 0–1 | Cementarnica |
| Galeb | 0–6 | Vardar |
| BSK Bistrica | 3–1 | Balkan |
| Osogovo | 2–2 (3–4 p) | Bashkimi |
| Povardarie | 0–11 | Sileks |
| Bitola | 0–2 | Sasa |
| Belasica | 1–2 | Makedonija G.P. |
| Arsimi | 3–0 (w/o) | Kumanovo |
| Butel | 0–1 | Pobeda |
| Bregalnica Shtip | 2–0 | Tikvesh |
| Novaci | 0–1 | Rabotnichki Kometal |
| Ohrid 96 | 4–0 | Skopje |
| Udarnik | 1–2 | Napredok |
| Borec MHK | 0–1 | Metalurg Veles |
| Madzhari Solidarnost | 0–3 | Sloga Jugomagnat |
| Bregalnica Delchevo | 0–2 | Pelister |

## Group stage
### Group 1

| Pos | Team | Pld | W | D | L | GF | GA | GD | Pts | Qualification | SLO | RAB | OHR | ARS |
| 1 | Sloga Jugomagnat | 6 | 4 | 1 | 1 | 20 | 11 | +9 | 13 | Quarter-finals | — | 2–2 | 6–3 | 5–0 |
| 2 | Rabotnichki | 6 | 3 | 2 | 1 | 19 | 11 | +8 | 11 | Quarter-finals | 3–1 | — | 1–1 | 9–3 |
| 3 | Ohrid 96 | 6 | 3 | 1 | 2 | 19 | 12 | +7 | 10 | | 3–6 | 2–1 | — | 5–0 |
| 4 | Arsimi | 6 | 0 | 0 | 6 | 7 | 31 | −24 | 0 | | 1–3 | 2–3 | 1–6 | — |

### Group 2

| Pos | Team | Pld | W | D | L | GF | GA | GD | Pts | Qualification | CEM | SIL | SAS | MET |
| 1 | Cementarnica | 6 | 4 | 2 | 0 | 18 | 4 | +14 | 14 | Quarter-finals | — | 3–1 | 1–1 | 7–0 |
| 2 | Sileks | 6 | 4 | 0 | 2 | 22 | 7 | +15 | 12 | Quarter-finals | 1–3 | — | 8–0 | 5–0 |
| 3 | Sasa | 6 | 2 | 2 | 2 | 8 | 11 | −3 | 8 | | 0–0 | 0–2 | — | 4–0 |
| 4 | Metalurg Veles | 6 | 0 | 0 | 6 | 2 | 28 | −26 | 0 | | 1–4 | 1–5 | 0–3 | — |

### Group 3

| Pos | Team | Pld | W | D | L | GF | GA | GD | Pts | Qualification | POB | PEL | BAS | BSK |
| 1 | Pobeda | 6 | 5 | 0 | 1 | 33 | 6 | +27 | 15 | Quarter-finals | — | 5–1 | 4–1 | 9–0 |
| 2 | Pelister | 6 | 4 | 0 | 2 | 22 | 12 | +10 | 12 | Quarter-finals | 2–1 | — | 5–0 | 5–1 |
| 3 | Bashkimi | 6 | 3 | 0 | 3 | 9 | 15 | −6 | 9 | | 0–5 | 3–1 | — | 3–0 |
| 4 | BSK Bistrica | 6 | 0 | 0 | 6 | 5 | 36 | −31 | 0 | | 2–9 | 2–8 | 0–2 | — |

### Group 4

| Pos | Team | Pld | W | D | L | GF | GA | GD | Pts | Qualification | VAR | MAK | NAP | BRE |
| 1 | Vardar | 6 | 5 | 0 | 1 | 14 | 6 | +8 | 15 | Quarter-finals | — | 0–2 | 4–3 | 5–0 |
| 2 | Makedonija G.P. | 6 | 4 | 1 | 1 | 8 | 3 | +5 | 13 | Quarter-finals | 1–2 | — | 2–1 | 2–0 |
| 3 | Napredok | 6 | 1 | 1 | 4 | 5 | 11 | −6 | 4 | | 0–2 | 0–0 | — | 1–0 |
| 4 | Bregalnica Shtip | 6 | 1 | 0 | 5 | 3 | 10 | −7 | 3 | | 0–1 | 0–1 | 3–0 | — |

## Quarter-finals

The first legs were played on 15 March and second were played on 22 March 2000.
| Team 1 | Agg.Tooltip Aggregate score | Team 2 | 1st leg | 2nd leg |
| Rabotnichki Kometal | 3–2 | Cementarnica | 1–1 | 2–1 |
| Sileks | 0–4 | Sloga Jugomagnat | 0–1 | 0–3 |
| Makedonija G.P. | 2–3 | Pobeda | 0–0 | 2–3 |
| Pelister | 3–1 | Vardar | 1–0 | 2–1 |

## Semi-finals

The first legs were played on 5 April and the second were played on 19 and 20 April 2000.

### Summary

| Team 1 | Agg.Tooltip Aggregate score | Team 2 | 1st leg | 2nd leg |
| Pelister | 3–4 | Pobeda | 2–2 | 1–2 |
| Rabotnichki Kometal | 2–4 | Sloga Jugomagnat | 1–1 | 1–3 |

### Matches

Pobeda won 4–3 on aggregate.
Sloga Jugomagnat won 4–2 on aggregate.