| Matches: 1899 | 1900 | League Tables: 1899-1900 | Forum |
1st Round (13 January 1900):
Abercorn Paisley 5-2 Ayr Parkhouse
Airdrieonians 0-1 Clyde
Celtic 7-1 FC Bo'ness
Dundee FC 8-0 Douglas Wanderers
Forfar Athletic 3-4 Motherwell
Forres Mechanics 1-1 Orion
Galston 1-2 Partick Thistle
Hamilton Academical 2-3 Hibernian Edinburgh
Heart of Midlothian 0-0 St.Mirren Paisley
Kilmarnock 2-0 E.Stirlingshire Falkirk
Maybole 4-2 Wishaw Thistle
Port Glasgow Athletic 7-1 Falkirk
Queen's Park Glasgow 3-0 Leith Athletic
Rangers 4-2 Morton Greenock
St.Bernard's Edinburgh 1-0 Arbroath
Third Lanark Glasgow 5-1 Raith Rovers Kirkcaldy
Replays 1st Round (20 January 1900):
Orion 4-1 Forres Mechanics
St.Mirren Paisley 0-3 Heart of Midlothian
2nd Round (27 January 1900):
Dundee FC 3-3 Clyde
Heart of Midlothian 1-1 Hibernian Edinburgh
Kilmarnock 10-1 Orion
Partick Thistle 2-1 St.Bernard's Edinburgh
Port Glasgow Athletic 1-5 Celtic
Queen's Park Glasgow 5-1 Abercorn Paisley
Rangers 12-0 Maybole
Third Lanark Glasgow 2-1 Motherwell
Replays 2nd Round (3 February 1900):
Clyde 0-3 Dundee FC (17 Feb)
Hibernian Edinburgh 1-2 Heart of Midlothian
Quarter Finals (10 February 1900):
Celtic 4-0 (17 Feb) Kilmarnock
Partick Thistle(2) 1-6 (17 Feb) Rangers
Queen's Park Glasgow 1-0 (24 Feb) Dundee FC
Third Lanark Glasgow 1-2 Heart of Midlothian
Semi Finals (10 March 1900):
Queen's Park Glasgow 2-1 Heart of Midlothian
Rangers 2-2 Celtic (24 Feb)
Replay Semi Finals (10 March 1900):
Celtic 4-0 Rangers
Final (Ibrox Park, 14 May 1900):
Celtic 4-3 Queen's Park Glasgow
Cup Winners: Celtic.