| First round |
| 7 September 1889 | 3rd Lanark Rifle Volunteers | 3 | - | 2 | Partick Thistle | |
| Walkover | Aberdeen | | | | Portland Lybster | Scratched |
| 7 September 1889 | Airdriehill | 5 | - | 6 | Motherwell | |
| 7 September 1889 | Alloa Athletic | 5 | - | 1 | Denny | |
| 7 September 1889 | Alva | 3 | - | 6 | King's Park | |
| 7 September 1889 | Arbroath | 3 | - | 5 | Dundee Harp | |
| 7 September 1889 | Armadale | 2 | - | 3 | Hibernian | |
| 7 September 1889 | Arthurlie | 2 | - | 4 | St Mirren | |
| 7 September 1889 | Ayr | 16 | - | 0 | Beith | |
| 7 September 1889 | Bathgate Rovers | 3 | - | 3 | Champfleurie | |
| 7 September 1889 | Bellstane Birds | 6 | - | 3 | Norton Park | |
| 7 September 1889 | Blairgowrie Our Boys | 3 | - | 5 | St Johnstone | |
| 7 September 1889 | Bowling | 1 | - | 8 | Renton | |
| 7 September 1889 | Broughty | 1 | - | 6 | Dundee East End | |
| 7 September 1889 | Bute Rangers | 1 | - | 2 | Kilbarchan | |
| 7 September 1889 | Cambuslang St Bride's | 1 | - | 6 | Airdrieonians | |
| 7 September 1889 | Carfin Shamrock | 4 | - | 0 | Albion Rovers | |
| 7 September 1889 | Carrington | 0 | - | 3 | Maryhill | |
| 7 September 1889 | Celtic | 0 | - | 0 | Queen's Park | |
| Scratched | Clydebank | | | | Vale of Leven Wanderers | Walkover |
| 7 September 1889 | Clydesdale | 1 | - | 6 | Cambuslang | |
| 7 September 1889 | Cowdenbeath | 8 | - | 0 | Kirkcaldy Wanderers | |
| 7 September 1889 | Cowlairs | 21 | - | 1 | Victoria | |
| 7 September 1889 | Dairy | 3 | - | 3 | Kilbirnie | |
| 7 September 1889 | Dunblane | 4 | - | 1 | Caledonian Rangers | |
| 7 September 1889 | Dundee Our Boys | 6 | - | 3 | Strathmore | |
| 7 September 1889 | Dunipace | 2 | - | 3 | Laurieston | |
| 7 September 1889 | Duntocher Harp | 5 | - | 0 | Smithstown Hibernian | |
| 7 September 1889 | Fair City Athletic | 8 | - | 0 | Coupar Angus | |
| 7 September 1889 | Gairdoch | 0 | - | 7 | East Stirlingshire | |
| 7 September 1889 | Glasgow Hibernian | 1 | - | 3 | Thistle | |
| Walkover | Greenock Abstainers | | | | Renfrew | Scratched |
| 7 September 1889 | Hamilton Academical | 0 | - | 5 | Wishaw Thistle | |
| 7 September 1889 | Irvine | 2 | - | 2 | Lugar Boswell | |
| 7 September 1889 | Jamestown | 2 | - | 4 | Methlan Park | |
| Walkover | Kelvinside Athletic | | | | Southern Athletic | Scratched |
| 7 September 1889 | Kilmarnock | 2 | - | 3 | Annbank | |
| 7 September 1889 | Kilsyth Wanderers | 5 | - | 1 | Stenhousemuir | |
| 7 September 1889 | Lassodie | 3 | - | 2 | Burntisland Thistle | |
| 7 September 1889 | Leith Athletic | 6 | - | 2 | Adventurers | |
| 7 September 1889 | Lindertis | 0 | - | 5 | Wanderers | |
| 7 September 1889 | Linthouse | 7 | - | 2 | Fairfield | |
| 7 September 1889 | Lochee | 4 | - | 1 | Brechin | |
| 31 August 1889 | Lochwinnoch | 1 | - | 10 | Abercorn | |
| 7 September 1889 | Mauchline | 1 | - | 4 | Newmilns | |
| 7 September 1889 | Maybole | 6 | - | 6 | Ayr Athletic | |
| 7 September 1889 | Mid-Annandale | 3 | - | 11 | 5th Kirkcudbrightshire Rifle Volunteers | |
| 7 September 1889 | Moffat | 8 | - | 0 | Dumfries | |
| 7 September 1889 | Montrose | 2 | - | 4 | Forfar Athletic | |
| 7 September 1889 | Morton | 8 | - | 0 | Carlton | |
| 7 September 1889 | Mossend Swifts | 6 | - | 0 | Bo'ness | |
| 7 September 1889 | Newton Stewart Athletic | 3 | - | 4 | Queen of the South Wanderers | |
| 7 September 1889 | Oban | 5 | - | 2 | Oban Rangers | |
| 7 September 1889 | Old Kilpatrick | 1 | - | 7 | Dumbarton Union | |
| 7 September 1889 | Orion | 3 | - | 1 | Victoria United | |
| 7 September 1889 | Pollokshaws | 3 | - | 1 | Dykebar | |
| 7 September 1889 | Pollokshaws Harp | 1 | - | 7 | 1st Renfrew Rifle Volunteers | |
| 7 September 1889 | Port Glasgow Athletic | 2 | - | 1 | Neilston | |
| 7 September 1889 | Raith Rovers | 1 | - | 2 | Dunfermline Athletic | |
| 7 September 1889 | Rangers | 6 | - | 2 | United Abstainers Athletic | |
| 7 Septemer 1889 | Royal Albert | 12 | - | 0 | Whifflet Shamrock | |
| 7 September 1889 | Rutherglen | 2 | - | 8 | Uddingston | |
| 7 September 1889 | Shettleston | 1 | - | 7 | Battlefield | |
| 7 September 1889 | Slamannan | 0 | - | 8 | Grangemouth | |
| 7 September 1889 | St Bernard's | 0 | - | 3 | Heart of Midlothian | |
| 7 September 1889 | Stevenston Thistle | 4 | - | 1 | Kilmarnock Athletic | |
| 7 September 1889 | Stewarton Cunninghame | 0 | - | 5 | Hurlford | |
| Walkover | Summerton Athletic | | | | Temperance Athletic | Scratched |
| Walkover | Thornliebank | | | | Johnstone Harp | Scratched |
| 7 September 1889 | Tillicoultry | 1 | - | 11 | Falkirk | |
| Walkover | Vale of Athole | | | | Crieff | Scratched |
| 7 September 1889 | Vale of Bannock | 3 | - | 6 | Campsie | |
| 7 September 1889 | Vale of Leven | 0 | - | 0 | Dumbarton | |
| 31 August 1889 | West Calder | 2 | - | 9 | Broxburn | |
| 7 September 1889 | Whitefield | 0 | - | 5 | Northern | |
| Bye | Camelon | | | | | |
| Bye | Clyde | | | | | |
| Bye | Dumfries Harp | | | | | |
| Bye | Edinburgh University | | | | | |
| Bye | Kirkintilloch Athletic | | | | | |
| Bye | Lanemark | | | | | |
| Bye | Lochgilphead | | | | | |
| Replays |
| 14 September 1889 | Ayr Athletic | 3 | - | 1 | Maybole | |
| Walkover | Champfleurie | | | | Bathgate Rovers | |
| 14 September 1889 | Dumbarton | 1 | - | 1 | Vale of Leven | Both teams qualified for next round |
| 14 September 1889 | Kilbirnie | 5 | - | 2 | Dairy | |
| 14 September 1889 | Lugar Boswell | 8 | - | 0 | Irvine | |
| 14 September 1889 | Queen's Park | 2 | - | 1 | Celtic | |
| Second round |
| 28 September 1889 | 1st Renfrew Rifle Volunteers | 2 | - | 10 | Morton | |
| 28 September 1889 | 3rd Lanark Rifle Volunteers | 9 | - | 3 | Maryhill | |
| 28 September 1889 | Abercorn | 10 | - | 1 | Thornliebank | |
| 28 September 1889 | Aberdeen | 2 | - | 1 | Orion | |
| 28 September 1889 | Airdrieonians | 5 | - | 2 | Uddingston | |
| 28 September 1889 | Battlefield | 0 | - | 2 | Thistle | |
| 28 September 1889 | Bellstane Birds | 1 | - | 4 | Heart of Midlothian | |
| 28 September 1889 | Broxburn | 2 | - | 2 | Leith Athletic | |
| 28 September 1889 | Camelon | 4 | - | 4 | Grangemouth | |
| 28 September 1889 | Campsie | 3 | - | 7 | Alloa Athletic | |
| 28 September 1889 | Carfin Shamrock | 6 | - | 2 | Motherwell | |
| 28 September 1889 | Clyde | 1 | - | 2 | Northern | |
| 28 September 1889 | Cowlairs | 1 | - | 1 | Linthouse | |
| 28 September 1889 | Dumbarton Union | 5 | - | 2 | Kirkintilloch Athletic | |
| 28 September 1889 | Dumfries Harp | 1 | - | 5 | Queen of the South Wanderers | |
| 28 September 1889 | Dundee Harp | 5 | - | 6 | Dundee Our Boys | |
| Walkover | Dunfermline Athletic | | | | Dunfermline | Scratched |
| 28 September 1889 | Duntocher Harp | 3 | - | 4 | Vale of Leven Wanderers | |
| 28 September 1889 | Falkirk | 5 | - | 2 | King's Park | |
| 28 September 1889 | Hibernian | 4 | - | 3 | Mossend Swifts | |
| 28 September 1889 | Kelvinside Athletic | 0 | - | 13 | Rangers | |
| 28 September 1889 | Kilbirnie | 5 | - | 0 | Newmilns | |
| 28 September 1889 | Lanemark | 2 | - | 1 | Hurlford | |
| 28 September 1889 | Lassodie | 3 | - | 3 | Cowdenbeath | |
| 28 September 1889 | Laurieston | 1 | - | 4 | East Stirlingshire | |
| 28 September 1889 | Lochee | 1 | - | 7 | Forfar Athletic | |
| 28 September 1889 | Lugar Boswell | 0 | - | 2 | Ayr | |
| 28 September 1889 | Moffat | 4 | - | 1 | 5th Kirkcudbrightshire Rifle Volunteers | |
| Walkover | Oban | | | | Lochgilphead | Scratched |
| 28 September 1889 | Port Glasgow Athletic | 8 | - | 0 | Greenock Abstainers | |
| 28 September 1889 | Queen's Park | 11 | - | 0 | Summerton Athletic | |
| 28 September 1889 | Renton | 1 | - | 2 | Dumbarton | |
| 28 September 1889 | Royal Albert | 1 | - | 1 | Cambuslang | |
| 28 September 1889 | St Johnstone | 2 | - | 2 | Fair City Athletic | |
| 28 September 1889 | St Mirren | 6 | - | 0 | Kilbarchan | |
| 28 September 1889 | Stevenston Thistle | 3 | - | 2 | Annbank | |
| 28 September 1889 | Vale of Atholl | 4 | - | 9 | Dunblane | |
| 28 September 1889 | Vale of Leven | 4 | - | 1 | Methlan Park | |
| 28 September 1889 | Wanderers | 0 | - | 2 | Dundee East End | |
| Bye | Ayr Athletic | | | | | |
| Bye | Champfleurie | | | | | |
| Bye | Edinburgh University | | | | | |
| Bye | Kilsyth Wanderers | | | | | |
| Bye | Pollokshaws | | | | | |
| Bye | Wishaw Thistle | | | | | |
| Replays |
| 5 October 1889 | Cambuslang | 4 | - | 1 | Royal Albert | |
| Walkover | Cowdenbeath | | | | Lassodie | Scratched |
| 5 October 1889 | Fair City Athletic | 3 | - | 2 | St Johnstone | |
| 5 October 1889 | Grangemouth | 7 | - | 2 | Camelon | |
| 5 October 1889 | Leith Athletic | 2 | - | 1 | Broxburn | |
| 5 October 1889 | Linthouse | 3 | - | 2 | Cowlairs | |
| Third round |
| 19 October 1889 | Abercorn | 5 | - | 2 | Stevenston Thistle | |
| 19 October 1889 | Aberdeen | 5 | - | 3 | Forfar Athletic | |
| 19 October 1889 | Alloa Athletic | 3 | - | 0 | Oban | |
| 19 October 1889 | Champfleurie | 0 | - | 5 | Heart of Midlothian | |
| 19 October 1889 | Dumbarton | 1 | - | 1 | 3rd Lanark Rifle Volunteers | |
| 19 October 1889 | Dumbarton Union | 1 | - | 3 | Cambuslang | Match declared void |
| 19 October 1889 | Dunblane | 3 | - | 0 | Fair City Athletic | |
| 19 October 1889 | Dundee Our Boys | 2 | - | 3 | Dundee East End | |
| 19 October 1889 | Dunfermline Athletic | 4 | - | 4 | Hibernian | |
| 19 October 1889 | Edinburgh University | 0 | - | 9 | Leith Athletic | |
| 19 October 1889 | Falkirk | 1 | - | 6 | East Stirlingshire | |
| 19 October 1889 | Grangemouth | 2 | - | 2 | Kilsyth Wanderers | |
| 19 October 1889 | Lanemark | 4 | - | 3 | Ayr Athletic | |
| 19 October 1889 | Moffat | 0 | - | 0 | Queen of the South Wanderers | |
| 19 October 1889 | Morton | 1 | - | 4 | Ayr | |
| 19 October 1889 | Northern | 2 | - | 1 | Carfin Shamrock | Match declared void |
| 19 October 1889 | Port Glasgow Athletic | 3 | - | 4 | Kilbirnie | |
| 19 October 1889 | Queen's Park | 8 | - | 0 | Vale of Leven Wanderers | |
| 19 October 1889 | Rangers | 0 | - | 0 | Vale of Leven | |
| 19 October 1889 | St Mirren | 5 | - | 1 | Pollokshaws | |
| 19 October 1889 | Thistle | 2 | - | 2 | Airdrieonians | |
| 19 October 1889 | Wishaw Thistle | 8 | - | 5 | Linthouse | Wishaw Thistle disqualified; Linthouse reinstated |
| Bye | Cowdenbeath | | | | | |
| Replays |
| 26 October 1889 | 3rd Lanark Rifle Volunteers | 1 | - | 0 | Dumbarton | |
| 26 October 1889 | Airdrieonians | 3 | - | 1 | Thistle | |
| 2 November 1889 | Cambuslang | 6 | - | 0 | Dumbarton Union | |
| 26 October 1889 | Hibernian | 11 | - | 1 | Dunfermline Athletic | |
| 26 October 1889 | Kilsyth Wanderers | 0 | - | 1 | Grangemouth | |
| 2 November 1889 | Northern | 3 | - | 2 | Carfin Shamrock | |
| 26 October 1889 | Queen of the South Wanderers | 5 | - | 5 | Moffat | Both teams advanced to next round |
| 26 October 1889 | Vale of Leven | 3 | - | 2 | Rangers | |
| Fourth round |
| 9 November 1889 | 3rd Lanark Rifle Volunteers | 2 | - | 0 | Linthouse | |
| 9 November 1889 | Aberdeen | 1 | - | 13 | Queen's Park | |
| 9 November 1889 | Airdrieonians | 2 | - | 3 | Abercorn | |
| 9 November 1889 | Ayr | 2 | - | 2 | Leith Athletic | |
| 9 November 1889 | Dunblane | 4 | - | 6 | Cowdenbeath | |
| 9 November 1889 | Dundee East End | 3 | - | 2 | Cambuslang | Match declared void |
| 9 November 1889 | Grangemouth | 1 | - | 7 | Vale of Leven | |
| 9 November 1889 | Heart of Midlothian | 9 | - | 1 | Alloa Athletic | |
| 9 November 1889 | Kilbirnie | 5 | - | 2 | East Stirlingshire | |
| 9 November 1889 | Lanemark | 2 | - | 8 | St Mirren | |
| 9 November 1889 | Moffat | 4 | - | 2 | Carfin Shamrock | |
| 9 November 1889 | Queen of the South Wanderers | 3 | - | 7 | Hibernian | |
| Replays |
| 23 November 1889 | Dundee East End | 3 | - | 2 | Cambuslang | |
| 16 November 1889 | Leith Athletic | 4 | - | 1 | Ayr | |
| Fifth round |
| 30 November 1889 | Cowdenbeath | 2 | - | 8 | Abercorn | |
| 30 November 1889 | Moffat | 2 | - | 2 | Dundee East End | |
| 30 November 1889 | Queen's Park | 1 | - | 0 | St Mirren | |
| 30 November 1889 | Vale of Leven | 3 | - | 1 | Heart of Midlothian | |
| Bye | 3rd Lanark Rifle Volunteers | | | | | |
| Bye | Hibernian | | | | | |
| Bye | Kilbirnie | | | | | |
| Bye | Leith Athletic | | | | | |
| Replays |
| 7 December 1889 | Dundee East End | 5 | - | 1 | Moffat | |
| Quarter-finals |
| 21 December 1889 | Abercorn | 6 | - | 2 | Hibernian | |
| 21 December 1889 | Kilbirnie | 1 | - | 4 | 3rd Lanark Rifle Volunteers | |
| 21 December 1889 | Queen's Park | 1 | - | 0 | Leith Athletic | |
| 21 December 1889 | Vale of Leven | 4 | - | 0 | Dundee East End | |
| Semi-final |
| 18 January 1890 | Queen's Park | 2 | - | 0 | Abercorn | |
| 18 January 1890 | Vale of Leven | 3 | - | 0 | 3rd Lanark Rifle Volunteers | |
| Final |
15 February 1890 | Queen's Park | 1 | - | 1 | Vale of Leven | Played at Ibrox Park, Glasgow |
11,000 | Hamilton | | | | McLachlan | |
Replay |
| 22 February 1890 | Queen's Park | 2 | - | 1 | Vale of Leven | Played at Ibrox Park, Glasgow |
| 13,000 | Hamilton, Stewart | | | | Bruce | |
