| First round |
| 6 September 1890 | Abercorn | 8 | - | 0 | Irvine | |
| 6 September 1890 | Annan | 2 | - | 8 | Dumfries Wanderers | |
| 6 September 1890 | Arthurlie | 2 | - | 5 | St Mirren | |
| Walkover | Ayr | | | | Kilbarchan | Scratched |
| 6 September 1890 | Ayr Parkhouse | 3 | - | 2 | Kilbirnie | |
| 6 September 1890 | Bathgate Rovers | 3 | - | 2 | Dunfermline Athletic | |
| 6 September 1890 | Battlefield | 1 | - | 4 | 3rd Lanark Rifle Volunteers | |
| Walkover | Bo'ness | | | | Blair Adam | Scratched |
| 6 September 1890 | Brechin | 3 | - | 4 | Kirriemuir | |
| 6 September 1890 | Bridge of Allan | 7 | - | 2 | Southfield Rangers | |
| Walkover | Broxburn | | | | West Calder | Scratched |
| 6 September 1890 | Burnbank Swifts | 11 | - | 0 | United Abstainers | |
| 6 September 1890 | Burntisland Thistle | 4 | - | 2 | Bonnyrigg Rose | |
| 6 September 1890 | Caledonian | 2 | - | 1 | Victoria United | |
| 6 September 1890 | Cambuslang | 3 | - | 1 | Glasgow Wanderers | |
| 6 September 1890 | Camelon | 4 | - | 3 | Alloa Athletic | |
| 6 September 1890 | Campsie | 4 | - | 1 | Laurieston | |
| 6 September 1890 | Campsie Hibernian | 3 | - | 6 | Clydebank Athletic | |
| Walkover | Carlton | | | | Lugar | Scratched |
| 6 September 1890 | Carrington | 1 | - | 2 | Albion Rovers | |
| Scratched | Cartha | | | | Carfin Shamrock | Walkover |
| 6 September 1890 | Cathcart | 5 | - | 3 | Pollokshaws Harp | |
| 6 September 1890 | Celtic | 1 | - | 0 | Rangers | |
| 6 September 1890 | Clackmannan | 9 | - | 0 | Milton of Campsie | |
| 6 September 1890 | Clyde | 7 | - | 2 | Whitefield | |
| 6 September 1890 | Cowdenbeath | 10 | - | 1 | Linlithgow Athletic | |
| 6 September 1890 | Cowlairs | 1 | - | 3 | Airdrieonians | |
| Walkover | Crieff | | | | Vale of Atholl | Scratched |
| 6 September 1890 | Dalry | 5 | - | 2 | Pollokshaws | |
| 6 September 1890 | Denny | 0 | - | 4 | Alva | |
| 6 September 1890 | Douglas Rovers | 0 | - | 5 | 5th Kirkcudbrightshire Rifle Volunteers | |
| 6 September 1890 | Dundee Wanderers | 3 | - | 3 | Arbroath | |
| Scratched | Dunipace | | | | Vale of Leven Wanderers | Walkover |
| 6 September 1890 | East Stirlingshire | 8 | - | 2 | Grangemouth | |
| 6 September 1890 | Fair City Athletic | 7 | - | 3 | Dunblane | |
| 6 September 1890 | Forfar Athletic | 2 | - | 7 | Dundee Our Boys | |
| 6 September 1890 | Greenock Abstainers | 0 | - | 13 | Newmilns | |
| Walkover | Hamilton Academical | | | | Linthouse | Scratched |
| 6 September 1890 | Heart of Midlothian | 7 | - | 2 | Raith Rovers | |
| 6 September 1890 | Inveraray | 4 | - | 1 | Lochgilphead | |
| 6 September 1890 | Inverness Thistle | 2 | - | 4 | Inverness Caledonian | |
| 6 September 1890 | Kelvinside Athletic | 1 | - | 1 | Glasgow Hibernian | |
| 6 September 1890 | Kilmarnock | 4 | - | 4 | Annbank | |
| 6 September 1890 | Kilsyth Wanderers | 2 | - | 1 | Renton | |
| 6 September 1890 | Kirkcaldy Wanderers | 3 | - | 4 | Hibernian | |
| 6 September 1890 | Kirkintilloch Athletic | 2 | - | 2 | Clydebank | |
| Walkover | Lanemark | | | | Dykebar | Scratched |
| 6 September 1890 | Leith Athletic | 3 | - | 2 | Annandale | |
| Scratched | Lochee | | | | Dundee Harp | Walkover |
| Walkover | Maryhill | | | | Southern Athletic | Scratched |
| 6 September 1890 | Mauchline | 1 | - | 3 | Kilmarnock Athletic | |
| 6 September 1890 | Maybole | 3 | - | 4 | Hurlford | |
| 6 September 1890 | Methlan Park | 1 | - | 0 | King's Park | |
| 6 September 1890 | Mid Annandale | 15 | - | 1 | Rising Thistle | |
| 6 September 1890 | Montrose | 7 | - | 1 | Broughty | |
| 6 September 1890 | Morton | 7 | - | 2 | Ayr Athletic | |
| Walkover | Mossend Swifts | | | | Lassodie | Scratched |
| 6 September 1890 | Motherwell Shamrock | 3 | - | 7 | Fairfield | |
| 6 September 1890 | Neilston | 7 | - | 3 | Bute Rangers | |
| 6 September 1890 | Newton Stewart Athletic | 0 | - | 9 | Dumfries | |
| 6 September 1890 | Northern | 5 | - | 0 | Clydesdale | Match declared void after protest |
| 6 September 1890 | Oban | 3 | - | 0 | Oban Rangers | |
| 6 September 1890 | Old Kilpatrick | 1 | - | 6 | Jamestown | |
| 6 September 1890 | Orion | 1 | - | 5 | Aberdeen | |
| 6 September 1890 | Penicuik Athletic | 5 | - | 3 | Champfleurie | |
| 6 September 1890 | Port Glasgow Athletic | 0 | - | 2 | Monkcastle | |
| 6 September 1890 | Royal Albert | 5 | - | 4 | Motherwell | |
| Walkover | Rutherglen | | | | St Bride's | Scratched |
| 6 September 1890 | Saltcoats Victoria | 4 | - | 3 | Lochwinnoch | |
| 6 September 1890 | Slamannan | 6 | - | 2 | Gairdoch | |
| 6 September 1890 | Smithston Hibernian | 2 | - | 8 | Dumbarton | |
| 6 September 1890 | St Bernard's | 7 | - | 0 | Adventurers | St Bernard's disqualified after protest |
| 6 September 1890 | St Johnstone | 2 | - | 2 | Coupar Angus | Coupar Angus disqualified after protest |
| Scratched | Stenhousemuir | | | | Vale of Leven | Walkover |
| 6 September 1890 | Stevenston Thistle | 9 | - | 2 | Stewarton Cunninghame | |
| Walkover | Stranraer | | | | Moffat | Scratched |
| Walkover | Strathmore | | | | East End | Scratched |
| 6 September 1890 | Thistle | 3 | - | 5 | Queen's Park | |
| 6 September 1890 | Tillicoultry | 1 | - | 5 | Dalmuir Thistle | |
| 6 September 1890 | Uddingston | 6 | - | 0 | Hamilton Harp | |
| 6 September 1890 | Union Dumbarton | 12 | - | 1 | Grasshoppers | |
| Walkover | Vale of Bannock | | | | Falkirk | Scratched |
| Scratched | Whifflet Shamrock | | | | Summerton Athletic | Walkover |
| 6 September 1890 | Wishaw Thistle | 3 | - | 2 | Partick Thistle | |
| Bye | Beith | | | | | |
| Bye | Bellstane Birds | | | | | |
| Bye | Edinburgh University | | | | | |
| Bye | Glengowan | | | | | |
| Bye | Portland Lybstor | | | | | |
| Replays |
| 13 September 1890 | Annbank | 6 | - | 2 | Kilmarnock | |
| 13 September 1890 | Arbroath | 4 | - | 1 | Dundee Wanderers | |
| 13 September 1890 | Clydebank | 4 | - | 3 | Kirkintilloch Athletic | |
| 13 September 1890 | Glasgow Hibernian | 5 | - | 1 | Kelvinside Athletic | |
| 20 September 1890 | Northern | 7 | - | 1 | Clydesdale | |
| Second round |
| 27 September 1890 | 3rd Lanark Rifle Volunteers | 8 | - | 1 | Kilmarnock Athletic | |
| 27 September 1890 | 5th Kirkcudbrightshire Rifle Volunteers | 9 | - | 1 | Mid-Annandale | Mid-Annandale walked off in protest |
| 27 September 1890 | Abercorn | 12 | - | 0 | Cathcart | |
| 27 September 1890 | Aberdeen | 8 | - | 0 | Caledonian | |
| Walkover | Adventurers | | | | Vale of Leven Wanderers | Scratched |
| 27 September 1890 | Airdrieonians | 3 | - | 1 | Annbank | |
| 27 September 1890 | Ayr Parkhouse | 1 | - | 2 | Summerton Athletic | |
| 27 September 1890 | Bathgate Rovers | 6 | - | 2 | Union | |
| 27 September 1890 | Beith | 2 | - | 4 | Cambuslang | |
| 11 October 1890 | Bo'ness | 7 | - | 0 | Bellstane Birds | |
| 27 September 1890 | Bridge of Allan | 1 | - | 5 | Vale of Leven | |
| 27 September 1890 | Broxburn | 5 | - | 2 | Clackmannan | |
| 27 September 1890 | Burnbank Swifts | 2 | - | 1 | Stevenston Thistle | Match declared void after protest |
| 27 September 1890 | Camelon | 2 | - | 1 | Alva | |
| 27 September 1890 | Campsie | 4 | - | 4 | East Stirlingshire | |
| Scratched | Carlton | | | | Glengowan | Walkover |
| 27 September 1890 | Celtic | 2 | - | 2 | Carfin Shamrock | |
| 27 September 1890 | Clyde | 4 | - | 3 | Hurlford | |
| 27 September 1890 | Clydebank Athletic | 3 | - | 5 | Kilsyth Wanderers | |
| 27 September 1890 | Crieff | 0 | - | 11 | Fair City Athletic | |
| 27 September 1890 | Dalmuir Thistle | 5 | - | 7 | Cowdenbeath | |
| 27 September 1890 | Dumfries Wanderers | 6 | - | 5 | Dumfries | |
| 27 September 1890 | Dundee East End | 4 | - | 2 | St Johnstone | |
| 27 September 1890 | Dundee Harp | 1 | - | 5 | Arbroath | |
| 27 September 1890 | Fairfield | 2 | - | 5 | Royal Albert | |
| Walkover | Heart of Midlothian | | | | Burntisland Thistle | Scratched |
| 27 September 1890 | Hibernian | 1 | - | 9 | Dumbarton | |
| 27 September 1890 | Inveraray | 4 | - | 2 | Oban | |
| Walkover | Inverness Caledonian | | | | Portland Lybster | Scratched |
| 27 September 1890 | Jamestown | 2 | - | 5 | Mossend Swifts | |
| 27 September 1890 | Kirriemuir | 0 | - | 3 | Montrose | |
| 27 September 1890 | Leith Athletic | 7 | - | 2 | Falkirk | |
| 27 September 1890 | Linthouse | 7 | - | 2 | Maryhill | |
| 27 September 1890 | Monkcastle | 4 | - | 3 | Dalry | |
| 27 September 1890 | Morton | 3 | - | 2 | Neilston | |
| 27 September 1890 | Newmilns | 2 | - | 2 | Uddingston | |
| 27 September 1890 | Penicuik Athletic | 3 | - | 4 | Methlan Park | |
| 27 September 1890 | Queen's Park | 5 | - | 1 | Northern | |
| 27 September 1890 | Rutherglen | 1 | - | 3 | Ayr | |
| 27 September 1890 | Saltcoats Victoria | 3 | - | 2 | Lanemark | |
| 27 September 1890 | Slamannan | 5 | - | 2 | Clydebank | Clydebank protested, match declared void |
| 27 September 1890 | St Mirren | 5 | - | 1 | Albion Rovers | |
| 27 September 1890 | Wishaw Thistle | 4 | - | 1 | Glasgow Hibernian | |
| Bye | Dundee Our Boys | | | | | |
| Bye | Edinburgh University | | | | | |
| Bye | Stranraer | | | | | |
| Replays |
| 11 October 1890 | Burnbank Swifts | 3 | - | 0 | Stevenston Thistle | |
| 4 October 1890 | Campsie | 1 | - | 3 | East Stirlingshire | |
| 4 October 1890 | Carfin Shamrock | 1 | - | 3 | Celtic | |
| 11 October 1890 | Slamannan | 3 | - | 5 | Clydebank | |
| 4 October 1890 | Uddingston | 5 | - | 1 | Newmilns | |
| Third round |
| 18 October 1890 | 3rd Lanark Rifle Volunteers | 8 | - | 1 | Summerton Athletic | |
| 18 October 1890 | Airdrieonians | 8 | - | 0 | Glengowan | |
| 18 October 1890 | Bathgate Rovers | 6 | - | 0 | Broxburn | |
| 18 October 1890 | Bo'ness | 1 | - | 1 | Mossend Swifts | |
| 18 October 1890 | Cambuslang | 1 | - | 2 | St Mirren | |
| 18 October 1890 | Clyde | 3 | - | 4 | Ayr | |
| 18 October 1890 | Dumbarton | 6 | - | 0 | Clydebank | |
| Walkover | Dumfries Wanderers | | | | Stranraer | Scratched |
| 18 October 1890 | Dundee Our Boys | 4 | - | 0 | Dundee East End | |
| 18 October 1890 | East Stirlingshire | 3 | - | 3 | Camelon | |
| 18 October 1890 | Edinburgh University | 3 | - | 2 | Cowdenbeath | |
| 18 October 1890 | Inverness Caledonian | 6 | - | 2 | Aberdeen | |
| 18 October 1890 | Kilsyth Wanderers | 0 | - | 8 | Vale of Leven | |
| 18 October 1890 | Leith Athletic | 12 | - | 0 | Adventurers | |
| 18 October 1890 | Linthouse | 3 | - | 4 | Abercorn | |
| 18 October 1890 | Methlan Park | 0 | - | 3 | Heart of Midlothian | |
| 18 October 1890 | Monkcastle | 1 | - | 7 | Burnbank Swifts | |
| 18 October 1890 | Montrose | 4 | - | 1 | Fair City Athletic | |
| 18 October 1890 | Morton | 10 | - | 0 | Inveraray | |
| 18 October 1890 | Queen's Park | 6 | - | 0 | Uddingston | |
| 18 October 1890 | Royal Albert | 6 | - | 2 | Saltcoats Victoria | |
| 18 October 1890 | Wishaw Thistle | 2 | - | 6 | Celtic | |
| Bye | 5th Kirkcudbrightshire Rifle Volunteers | | | | | |
| Bye | Arbroath | | | | | |
| Replays |
| 25 October 1890 | Camelon | 6 | - | 10 | East Stirlingshire | |
| 25 October 1890 | Mossend Swifts | 9 | - | 1 | Bo'ness | |
| Fourth round |
| 8 November 1890 | 5th Kirkcudbrightshire Rifle Volunteers | 6 | - | 2 | Arbroath | |
| 8 November 1890 | Abercorn | 8 | - | 0 | Bathgate Rovers | |
| 8 November 1890 | Airdrieonians | 1 | - | 2 | St Mirren | |
| 8 November 1890 | Ayr | 3 | - | 4 | Heart of Midlothian | |
| 8 November 1890 | Dumbarton | 7 | - | 3 | Mossend Swifts | |
| 8 November 1890 | Dundee Our Boys | 1 | - | 3 | Celtic | |
| 8 November 1890 | East Stirlingshire | 2 | - | 0 | Inverness Caledonian | |
| 8 November 1890 | Edinburgh University | 0 | - | 7 | Queen's Park | |
| 8 November 1890 | Leith Athletic | 3 | - | 1 | Vale of Leven | |
| 8 November 1890 | Montrose | 0 | - | 3 | 3rd Lanark Rifle Volunteers | |
| 8 November 1890 | Morton | 6 | - | 4 | Dumfries Wanderers | |
| 8 November 1890 | Royal Albert | 1 | - | 0 | Burnbank Swifts | |
| Fifth round |
| 29 November 1890 | Celtic | 2 | - | 2 | Royal Albert | Match declared void |
| 29 November 1890 | Dumbarton | 2 | - | 0 | 5th Kirkcudbrightshire Rifle Volunteers | Match declared void |
| 29 November 1890 | Heart of Midlothian | 5 | - | 1 | Morton | |
| 6 December 1890 | St Mirren | 2 | - | 3 | Queen's Park | |
| Bye | 3rd Lanark Rifle Volunteers | | | | | |
| Bye | Abercorn | | | | | |
| Bye | East Stirlingshire | | | | | |
| Bye | Leith Athletic | | | | | |
| Replays |
| 6 December 1890 | Dumbarton | 8 | - | 0 | 5th Kirkcudbrightshire Rifle Volunteers | |
| 6 December 1890 | Royal Albert | 0 | - | 4 | Celtic | Match declared void - due to crowd trouble match abandoned |
2nd Replay |
| 13 December 1890 | Celtic | 2 | - | 0 | Royal Albert | Played at 1st Ibrox Park, Glasgow |
| Quarter-finals |
| 20 December 1890 | Dumbarton | 3 | - | 0 | Celtic | |
| 20 December 1890 | Heart of Midlothian | 3 | - | 1 | East Stirlingshire | |
| 20 December 1890 | Leith Athletic | 2 | - | 3 | Abercorn | |
| 10 January 1891 | Queen's Park | 1 | - | 1 | 3rd Lanark Rifle Volunteers | |
| Replay |
| 17 January 1891 | 3rd Lanark Rifle Volunteers | 2 | - | 2 | Queen's Park | |
| 2nd Replay |
| 24 January 1891 | 3rd Lanark Rifle Volunteers | 4 | - | 1 | Queen's Park | |
| Semi-final |
| 31 January 1891 | 3rd Lanark Rifle Volunteers | 1 | - | 4 | Heart of Midlothian | |
| 17 January 1891 | Dumbarton | 3 | - | 1 | Abercorn | |
| Final |
7 February 1891 | Heart of Midlothian | 1 | - | 0 | Dumbarton | Played at 2nd Hampden Park, Glasgow |
10,836 | Mason | | | | | |
