Ulster Senior Football Championship 1999
| 1st Round | Quarter-finals | Semi-finals | Final | Champions |
|
| Monaghan |
| | |
| v | Fermanagh |
| | |
| Fermanagh | v | Tyrone |
| Tyrone |
| Down | v | Down |
| v | Down |
| Antrim |
| Donegal | | v |  | Armagh |
| v | Armagh |
| Armagh | |
| Derry | v | Armagh |
| v | Derry |
| Cavan |
Dates & Venues
| Round | Date | Fixture | Venue |
| Round 1 | May 30 | Monaghan | 1-10 | 2-12 | Fermanagh | Clones |
| Quarter-final 1 | June 6 | Donegal | 2-9 | 1-12 | Armagh | Ballybofey |
| Quarter-final 1 Replay | June 13 | Armagh | 2-11 | 0-12 | Donegal | Clones |
| Quarter-final 2 | June 13 | Derry | 2-15 | 2-15 | Cavan | Derry |
| Quarter-final 2 Replay | June 20 | Derry | 2-14 | 0-5 | Cavan | Derry |
| Quarter-final 3 | June 20 | Down | 1-15 | 0-14 | Antrim | Newry |
| Quarter-final 4 | June 27 | Tyrone | 0-18 | 0-8 | Fermanagh | Omagh |
| Semi-final 1 | June 4 | Armagh | 1-10 | 0-12 | Derry | Clones |
| Semi-final 2 | July 4 | Down | 2-14 | 0-15 | Tyrone | Casement Park |
| Final | August 1 | Armagh | 3-12 | 0-10 | Down | Clones |
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