# 1999–2000 Irish Cup

The 1999–2000 Irish Cup was the 120th edition of the Irish Cup, Northern Ireland's premier football knock-out cup competition. It concluded on 6 May 2000 with the final.
Portadown were the defending champions, winning their 2nd Irish Cup last season after Cliftonville were disqualified from the 1999 final. This season Portadown reached the final again, but were defeated 1–0 by Glentoran, who won the cup for the 18th time.

## Results
### Preliminary round

| Team 1 | Score | Team 2 |
| 1st Bangor Old Boys | 1–2 | UUJ |
| Abbey Villa | 6–0 | Banbridge AFC |
| AFC Craigavon | 1–3 | Tandragee Rovers |
| Albert Foundry | 3–3 | Downshire Young Men |
| Ballycastle United | 2–5 | East Belfast |
| Ballymacash Rangers | 6–0 | Seapatrick |
| Ballynanhinch United | 2–4 | Laurelvale |
| Bridge End United | 0–2 | Dungiven Celtic |
| Comber Recreation | 4–0 | Bangor Amateurs |
| Harland & Wolff Sports | 2–2 | Barn United |
| Islandmagee | 5–2 | Oxford United Stars |
| Larne Tech Old Boys | 1–2 | Malachians |
| Magherafelt Sky Blues | 0–5 | Bessbrook United |
| Northern Telecom | 2–0 | Sirocco Works |
| Queen's University | 2–2 | Warrenpoint Town |
| Richhill | 0–3 | Draperstown Celtic |
| Roe Valley | 2–4 | Saintfield United |
| Shorts | 1–1 | Donard Hospital |
| UUC | 3–1 | Wellington Recreation |

#### Replays

| Team 1 | Score | Team 2 |
| Barn United | 5–1 | Harland & Wolff Sports |
| Donard Hospital | 0–3 | Shorts |
| Downshire Young Men | 0–1 | Albert Foundry |
| Warrenpoint Town | 1–2 | Queen's University |

### First round

| Team 1 | Score | Team 2 |
| Albert Foundry | 1–5 | Saintfield United |
| Ballymacash Rangers | 2–2 | Queen's University |
| Barn United | 1–2 | Draperstown Celtic |
| Bessbrook United | 2–1 | UUJ |
| Dungiven Celtic | 0–4 | East Belfast |
| Islandmagee | 1–6 | Comber Recreation |
| Laurelvale | 4–1 | Tandragee Rovers |
| Malachians | 0–0 | UUC |
| Northern Telecom | 1–1 | Shorts |

#### Replays

| Team 1 | Score | Team 2 |
| Queen's University | 1–2 | Ballymacash Rangers |
| Short Brothers | 0–6 | Northern Telecom |
| UUC | 3–4 | Malachians |

### Second round

| Team 1 | Score | Team 2 |
| East Belfast | 3–0 | Draperstown Celtic |
| Northern Telecom | 3–3 | Saintfield United |

#### Replay

| Team 1 | Score | Team 2 |
| Saintfield United | 2–3 | Northern Telecom |

### Third round

| Team 1 | Score | Team 2 |
| Ballymacash Rangers | 1–5 | Comber Recreation |
| East Belfast | 5–0 | Northern Telecom |
| Laurelvale | 0–4 | Bessbrook United |
| Malachians | 4–0 | Abbey Villa |

### Fourth round

| Team 1 | Score | Team 2 |
| Ards Rangers | 3–0 | Drumaness Mills |
| Banbridge AFC | 4–1 | Kilmore Recreation |
| Crumlin United | 3–3 | Harland & Wolff Welders |
| Donegal Celtic | 1–1 | Coagh United |
| Dundela | 1–3 | Ballinamallard United |
| East Belfast | 7–0 | Dromara Village |
| Killyleagh Youth | 2–0 | VIP Sport |
| Portstewart | 0–0 | Crewe United |

#### Replays

| Team 1 | Score | Team 2 |
| Donegal Celtic | 2–1 (a.e.t.) | Coagh United |
| Crewe United | 4–1 | Portstewart |
| Harland & Wolff Welders | 3–2 | Crumlin United |

### Fourth round (A)

| Team 1 | Score | Team 2 |
| Ards Rangers | 1–3 | Portstewart |
| Ballinamallard United | 4–1 | Malachians |
| Ballymoney United | 2–3 | Comber Recreation |
| Banbridge Town | 1–0 | Harland & Wolff Welders |
| Chimney Corner | 2–7 | Bessbrook United |
| Cookstown United | 1–2 | RUC |
| Donegal Celtic | 1–3 | Brantwood |
| Dunmurry Recreation | 1–5 | East Belfast |
| FC Enkalon | 3–2 | Moyola Park |
| Killyleagh Youth | 5–1 | Lurgan Celtic |

### Fifth round

| Team 1 | Score | Team 2 |
| Ballinamallard United | 1–2 | Killyleagh Youth |
| Banbridge Town | 3–2 | East Belfast |
| Bangor | 2–0 | Carrick Rangers |
| Brantwood | 2–3 | Bessbrook United |
| Cliftonville | 3–0 | Portstewart |
| Coleraine | 7–0 | Comber Recreation |
| Dungannon Swifts | 0–0 | Ards |
| Glenavon | 0–1 | Newry Town |
| Glentoran | 3–0 | Crusaders |
| Institute | 1–2 | RUC |
| Larne | 1–5 | Portadown |
| Limavady United | 0–2 | Armagh City |
| Linfield | 3–1 | FC Enkalon |
| Lisburn Distillery | 2–1 | Omagh Town |
| Loughgall | 0–1 | Ballymena United |
| Tobermore United | 4–2 | Ballyclare Comrades |

#### Replay

| Team 1 | Score | Team 2 |
| Ards | 0–1 (a.e.t.) | Dungannon Swifts |

### Sixth round

| Team 1 | Score | Team 2 |
| Armagh City | 2–2 | Glentoran |
| Ballymena United | 2–1 | Bessbrook United |
| Bangor | 3–3 | Coleraine |
| Dungannon Swifts | 4–0 | Tobermore United |
| Killyleagh Youth | 0–1 | Linfield |
| Lisburn Distillery | 3–0 | RUC |
| Newry Town | 3–0 | Banbridge Town |
| Portadown | 1–0 | Cliftonville |

#### Replays

| Team 1 | Score | Team 2 |
| Coleraine | 8–3 | Bangor |
| Glentoran | 4–0 | Armagh City |

### Quarter-finals

| Team 1 | Score | Team 2 |
| Coleraine | 1–0 | Ballymena United |
| Linfield | 2–2 | Dungannon Swifts |
| Lisburn Distillery | 0–2 | Portadown |
| Newry Town | 1–3 | Glentoran |

#### Replay

| Team 1 | Score | Team 2 |
| Dungannon Swifts | 1–2 (a.e.t.) | Linfield |

### Semi-finals

| Team 1 | Score | Team 2 |
| Coleraine | 0–0 | Portadown |
| Linfield | 2–3 | Glentoran |

#### Replay

| Team 1 | Score | Team 2 |
| Portadown | 1–0 | Coleraine |