| First round |
| Walkover | 5th Kirkcudbrightshire Rifle Volunteers | | | | Thornhill | Scratched |
| 11 September 1886 | Airdrieonians | 5 | - | 0 | Airdriehill | |
| 11 September 1886 | Albion Rovers | 5 | - | 1 | Clydesdale | |
| 11 September 1886 | Annbank | 3 | - | 4 | Kilbirnie | |
| 11 September 1886 | Arbroath | 20 | - | 0 | Orion | |
| 11 September 1886 | Ayr | 2 | - | 3 | Hurlford | |
| 11 September 1886 | Battlefield | 0 | - | 2 | Cowlairs | |
| 11 September 1886 | Bonhill | 8 | - | 1 | Kirkintilloch Central | |
| 11 September 1886 | Broxburn Shamrock | 1 | - | 2 | Mossend Swifts | |
| 11 September 1886 | Broxburn Thistle | 2 | - | 2 | Bellstane Birds | |
| Walkover | Burntisland Thistle | | | | Dunfermline | Scratched |
| 11 September 1886 | Cambuslang | 6 | - | 1 | Motherwell | |
| 11 September 1886 | Campsie | 10 | - | 0 | Dunipace | |
| 11 September 1886 | Carrick | 0 | - | 2 | Westbourne | |
| 11 September 1886 | Clyde | 5 | - | 1 | St Peter's | |
| Walkover | Coupar Angus | | | | Fair City Athletic | Scratched |
| 11 September 1886 | Dairy | 5 | - | 2 | Ayr Rovers | |
| 11 September 1886 | Dumbarton | 5 | - | 0 | Vale of Leven Hibernians | |
| 11 September 1886 | Dumbarton Athletic | 8 | - | 0 | Duntocher | |
| 11 September 1886 | Dunblane | 12 | - | 0 | Crieff | |
| Walkover | Dundee East End | | | | Aberdeen | Scratched |
| 18 September 1886 | Dundee Our Boys | 2 | - | 5 | Forfar Athletic | |
| 11 September 1886 | Dunfermline Athletic | 4 | - | 8 | Alloa Athletic | |
| 11 September 1886 | East Stirlingshire | 6 | - | 3 | Camelon | |
| 11 September 1886 | Edina | 1 | - | 7 | Heart of Midlothian | |
| 11 September 1886 | Grahamston | 0 | - | 2 | Laurieston | |
| 11 September 1886 | Greenock Rangers | 3 | - | 4 | 1st Renfrew Rifle Volunteers | 1st Renfrew RV disqualified, Greenock Rangers reinstated |
| Walkover | Hamilton Academical | | | | Wishaw Swifts | Scratched |
| 11 September 1886 | Hibernian | 6 | - | 1 | Durhamstown Rangers | |
| 11 September 1886 | Johnstone | 6 | - | 2 | Cartvale | |
| 11 September 1886 | Kelvinside Athletic | 1 | - | 2 | Whitefield | |
| Walkover | Kilmarnock | | | | Cumnock | Scratched |
| 11 September 1886 | King's Park | 1 | - | 3 | Falkirk | |
| Walkover | Lenzie | | | | Dunbritton | Scratched |
| 11 September 1886 | Lindertis | 3 | - | 4 | Dundee Harp | |
| 11 September 1886 | Linthouse | 4 | - | 0 | Southern Athletic | |
| 11 September 1886 | Lochwinnoch | 0 | - | 6 | Morton | |
| 11 September 1886 | Longcroft Thistle | 3 | - | 3 | Vale of Bannock | |
| Walkover | Lugar Boswell | | | | Maybole | Scratched |
| 11 September 1886 | Monkcastle | 1 | - | 3 | Lanemark | |
| Walkover | Newcastleton | | | | Norton Park | Scratched |
| 11 September 1886 | Northern | 1 | - | 4 | 3rd Lanark Rifle Volunteers | |
| Walkover | Oban | | | | Blairgowie Our Boys | Scratched |
| 11 September 1886 | Partick Thistle | 2 | - | 3 | Queen's Park | |
| Walkover | Pollokshaws Athletic | | | | Woodvale | |
| 11 September 1886 | Port Glasgow Athletic | 10 | - | 1 | Johnstone Harp | |
| Walkover | Queen of the South Wanderers | | | | Nithsdale | |
| 11 September 1886 | Rangers | 9 | - | 1 | Govan Athletic | |
| 11 September 1886 | Renfrew | 3 | - | 3 | Abercorn | |
| Walkover | Renton | | | | Kirkintilloch Harp | |
| 11 September 1886 | Rutherglen | 2 | - | 0 | Drumpelier | |
| 11 September 1886 | Shettleston | 3 | - | 3 | Carfin Shamrock | |
| 11 September 1886 | Slamannan | 4 | - | 3 | Avondale | |
| 11 September 1886 | St Andrew's | 2 | - | 5 | Pollokshields Athletic | Match declared void |
| 11 September 1886 | St Bernard's | 3 | - | 2 | Bo'ness | |
| 11 September 1886 | St Johnstone | 3 | - | 3 | Erin Rovers | |
| 11 September 1886 | St Mirren | 5 | - | 3 | Arthurlie | |
| 11 September 1886 | Strathmore (Arbroath) | 3 | - | 0 | Strathmore (Dundee) | |
| 11 September 1886 | Thistle | 13 | - | 0 | Blairvaddick | |
| 11 September 1886 | Thornliebank | 3 | - | 2 | Neilston | |
| 11 September 1886 | Tollcross | 0 | - | 3 | Royal Albert | Royal Albert disqualified, Tollcross reinstated |
| 11 September 1886 | Vale of Leven | 9 | - | 0 | Kirkintilloch Athletic | |
| 11 September 1886 | Vale of Leven Wanderers | 6 | - | 3 | Jamestown | |
| Walkover | Vale of Nith | | | | Vale of Annan | Scratched |
| 11 September 1886 | Wanderers | 2 | - | 7 | Broughty | |
| 11 September 1886 | West Calder | 1 | - | 3 | Armadale | |
| 11 September 1886 | Yoker | 4 | - | 2 | Dumbarton Union | |
| Bye | Caledonian Rangers | | | | | |
| Bye | Cambuslang Hibernian | | | | | |
| Bye | Cowdenbeath | | | | | |
| Bye | Dykehead | | | | | |
| Bye | Moffat | | | | | |
| Replays |
| 18 September 1886 | Abercorn | 9 | - | 0 | Renfrew | |
| 18 September 1886 | Broxburn Thistle | 4 | - | 1 | Bellstane Birds | |
| 18 September 1886 | Carfin Shamrock | 3 | - | 0 | Shettleston | |
| 18 September 1886 | Erin Rovers | 7 | - | 1 | St Johnston | |
| 25 September 1886 | St Andrew's | 4 | - | 1 | Pollokshields Athletic | |
| 18 September 1886 | Vale of Bannock | 2 | - | 0 | Longcroft Thistle | |
| Second round |
| 2 October 1886 | Abercorn | 8 | - | 2 | Greenock Rangers | |
| 2 October 1886 | Airdrieonians | 3 | - | 2 | Carfin Shamrock | Airdrieonians disqualified; Carfin Shamrock reinstated |
| 2 October 1886 | Albion Rovers | 7 | - | 0 | Dykehead | |
| 2 October 1886 | Bonhill | 1 | - | 2 | Jamestown | |
| 2 October 1886 | Broxburn Thistle | 1 | - | 2 | Heart of Midlothian | |
| 2 October 1886 | Caledonian Rangers | 4 | - | 4 | Erin Rovers | |
| 2 October 1886 | Cambuslang Hibernian | 3 | - | 1 | Hamilton Academical | |
| 2 October 1886 | Clyde | 4 | - | 3 | Cowlairs | |
| 2 October 1886 | Cowdenbeath | 3 | - | 3 | Burntisland Thistle | |
| 2 October 1886 | Dumbarton | 4 | - | 0 | Yoker | |
| 2 October 1886 | Dunblane | 8 | - | 1 | Oban | |
| 2 October 1886 | Dundee East End | 5 | - | 4 | Broughty | |
| Walkover | East Stirlingshire | | | | Vale of Bannock | Scratched |
| 2 October 1886 | Forfar Athletic | 2 | - | 5 | Arbroath | |
| 2 October 1886 | Hurlford | 3 | - | 2 | Kilbirnie | |
| 2 October 1886 | Johnstone | 4 | - | 0 | Pollokshaws Athletic | |
| 2 October 1886 | Kilmarnock | 10 | - | 2 | Lanemark | |
| 2 October 1886 | Laurieston | 1 | - | 3 | Falkirk | |
| 2 October 1886 | Lenzie | 0 | - | 13 | Vale of Leven | |
| 2 October 1886 | Linthouse | 1 | - | 4 | 3rd Lanark Rifle Volunteers | |
| 2 October 1886 | Lugar Boswell | 3 | - | 2 | Dairy | Match declared void |
| 2 October 1886 | Moffat | 3 | - | 5 | 5th Kirkcudbrightshire Rifle Volunteers | |
| 2 October 1886 | Mossend Swifts | 1 | - | 1 | Hibernian | |
| 2 October 1886 | Newcastleton | 1 | - | 5 | Armadale | |
| 2 October 1886 | Queen of the South Wanderers | 12 | - | 2 | Vale of Nith | |
| 2 October 1886 | Queen's Park | 7 | - | 0 | Whitefield | |
| 2 October 1886 | Rangers | 5 | - | 2 | Westbourne | |
| 2 October 1886 | Renton | 2 | - | 0 | Dumbarton Athletic | |
| 2 October 1886 | Rutherglen | 1 | - | 1 | Cambuslang | |
| 2 October 1886 | Slamannan | 0 | - | 3 | Campsie | |
| 2 October 1886 | St Mirren | 2 | - | 3 | Port Glasgow Athletic | |
| 2 October 1886 | Strathmore (Arbroath) | 3 | - | 3 | Dundee Harp | |
| 2 October 1886 | Thistle | 12 | - | 0 | St Andrew's | |
| 2 October 1886 | Thornliebank | 0 | - | 2 | Morton | |
| Bye | Alloa Athletic | | | | | |
| Bye | Coupar Angus | | | | | |
| Bye | St Bernard's | | | | | |
| Bye | Tollcross | | | | | |
| Replays |
| 9 October 1886 | Cambuslang | 6 | - | 1 | Rutherglen | |
| 16 October 1886 | Cowdenbeath | 3 | - | 1 | Burntisland Thistle | |
| 9 October 1886 | Dundee Harp | 3 | - | 3 | Strathmore (Arbroath) | Both teams qualified for next round |
| 9 October 1886 | Erin Rovers | 6 | - | 1 | Caledonian Rangers | |
| 9 October 1886 | Hibernian | 3 | - | 0 | Mossend Swifts | |
| 16 October 1886 | Lugar Boswell | 6 | - | 1 | Dairy | |
| Third round |
| 23 October 1886 | 3rd Lanark Rifle Volunteers | 3 | - | 1 | Renton | |
| 23 October 1886 | Abercorn | 1 | - | 5 | Port Glasgow Athletic | |
| 23 October 1886 | Albion Rovers | 4 | - | 2 | Thistle | |
| 23 October 1886 | Cambuslang Hibernian | 5 | - | 1 | Jamestown | |
| 23 October 1886 | Cowdenbeath | 6 | - | 1 | Alloa Athletic | |
| Walkover | Dumbarton | | | | Tollcross | Scratched |
| 23 October 1886 | Dundee East End | 3 | - | 3 | Dunblane | |
| 23 October 1886 | East Stirlingshire | 1 | - | 3 | Clyde | |
| 23 October 1886 | Erin Rovers | 3 | - | 2 | Coupar Angus | |
| 23 October 1886 | Falkirk | 3 | - | 8 | Queen's Park | |
| 23 October 1886 | Hibernian | 5 | - | 1 | Heart of Midlothian | |
| 23 October 1886 | Johnstone | 0 | - | 5 | Hurlford | |
| 23 October 1886 | Kilmarnock | 7 | - | 2 | Lugar Boswell | |
| 23 October 1886 | Queen of the South Wanderers | 6 | - | 3 | 5th Kirkcudbrightshire Rifle Volunteers | |
| 23 October 1886 | Rangers | 0 | - | 2 | Cambuslang | |
| 23 October 1886 | St Bernard's | 5 | - | 2 | Armadale | |
| 23 October 1886 | Strathmore (Arbroath) | 1 | - | 8 | Dundee Harp | |
| 23 October 1886 | Vale of Leven | 7 | - | 4 | Campsie | |
| Bye | Arbroath | | | | | |
| Bye | Carfin Shamrock | | | | | |
| Bye | Morton | | | | | |
| Replays |
| Walkover | Dundee East End | | | | Dunblane | Scratched |
| Fourth round |
| 13 November 1886 | Albion Rovers | 1 | - | 6 | Cambuslang | |
| 13 November 1886 | Cowdenbeath | 0 | - | 3 | Cambuslang Hibernian | |
| 6 November 1886 | Morton | 11 | - | 0 | Carfin Shamrock | |
| 13 November 1886 | Queen of the South Wanderers | 8 | - | 2 | Arbroath | |
| 13 November 1886 | St Bernard's | 5 | - | 1 | Erin Rovers | |
| Bye | 3rd Lanark Rifle Volunteers | | | | | |
| Bye | Clyde | | | | | |
| Bye | Dumbarton | | | | | |
| Bye | Dunblane | | | | | |
| Bye | Dundee Harp | | | | | |
| Bye | Hibernian | | | | | |
| Bye | Hurlford | | | | | |
| Bye | Kilmarnock | | | | | |
| Bye | Port Glasgow Athletic | | | | | |
| Bye | Queen's Park | | | | | |
| Bye | Vale of Leven | | | | | |
| Fifth round |
| 4 December 1886 | Clyde | 0 | - | 0 | 3rd Lanark Rifle Volunteers | |
| 4 December 1886 | Dundee Harp | 2 | - | 2 | Dumbarton | |
| 4 December 1886 | Hibernian | 7 | - | 3 | Queen of the South Wanderers | |
| 4 December 1886 | Hurlford | 5 | - | 1 | Morton | |
| 4 December 1886 | Kilmarnock | 6 | - | 0 | Dunblane | |
| 4 December 1886 | Port Glasgow Athletic | 6 | - | 2 | St Bernard's | |
| 4 December 1886 | Queen's Park | 1 | - | 1 | Cambuslang | |
| 27 November 1886 | Vale of Leven | 2 | - | 0 | Cambuslang Hibernian | |
| Replays |
| 11 December 1886 | 3rd Lanark Rifle Volunteers | 4 | - | 2 | Clyde | |
| 11 December 1886 | Cambuslang | 4 | - | 5 | Queen's Park | |
| Walkover | Dumbarton | | | | Dundee Harp | Scratched |
| Quarter-final |
| 25 December 1886 | 3rd Lanark Rifle Volunteers | 1 | - | 2 | Hibernian | |
| 25 December 1886 | Hurlford | 0 | - | 0 | Dumbarton | |
| 25 December 1886 | Kilmarnock | 0 | - | 5 | Queen's Park | |
| 25 December 1886 | Port Glasgow Athletic | 1 | - | 3 | Vale of Leven | |
| Replay |
| 8 January 1887 | Dumbarton | 1 | - | 2 | Hurlford | Match declared void |
| 2nd Replay |
| 22 January 1887 | Dumbarton | 3 | - | 1 | Hurlford | |
| Semi-final |
| 22 January 1887 | Hibernian | 3 | - | 1 | Vale of Leven | |
| 29 January 1887 | Queen's Park | 1 | - | 2 | Dumbarton | |
| Final |
12 February 1887 | Hibernian | 2 | - | 1 | Dumbarton | Played at Hampden Park, Glasgow |
15,000 | Montgomery, Groves | | | | Aitken | Referee: R Brown |