The 1999–2000 Scottish Cup was the 115th staging of Scotland's most prestigious football knockout competition, also known for sponsorship reasons as the Tennent's Scottish Cup. The Cup was won by Rangers who defeated Aberdeen 4–0 in the final.
| Tournament details | |
|---|---|
| Country | Scotland |
| Final positions | |
| Champions | Rangers |
| Runner-up | Aberdeen |
| Tournament statistics | |
| Top goal scorer(s) | Billy Dodds (5) |
First round
edit| Home team | Score | Away team |
|---|---|---|
| Threave Rovers | 1 – 7 | Stenhousemuir |
| Hamilton Academical | 1 – 2 | Clyde |
| Huntly | 0 – 1 | East Stirlingshire |
| Ross County | 2 – 2 | Forfar Athletic |
Replays
edit| Home team | Score | Away team |
|---|---|---|
| Forfar Athletic | 0 – 0 (4 – 2 pen.) |
Ross County |
Second round
edit| Home team | Score | Away team |
|---|---|---|
| Albion Rovers | 0 – 0 | Dalbeattie Star |
| Arbroath | 0 – 0 | Fraserburgh |
| Brechin City | 2 – 2 | Annan Athletic |
| Cowdenbeath | 2 – 3 | Clyde |
| Dumbarton | 0 – 2 | Stenhousemuir |
| Montrose | 1 – 3 | Queen of the South |
| Partick Thistle | 2 – 1 | East Stirlingshire |
| Peterhead | 2 – 1 | Forfar Athletic |
| Queen’s Park | 1 – 2 | Berwick Rangers |
| Stirling Albion | 2 – 1 | East Fife |
| Stranraer | 1 – 0 | Clachnacuddin |
| Whitehill Welfare | 2 – 2 | Alloa Athletic |
Replays
edit| Home team | Score | Away team |
|---|---|---|
| Annan Athletic | 2 – 3 | Brechin City |
| Dalbeattie Star | 1 – 5 | Albion Rovers |
| Fraserburgh | 1 – 3 | Arbroath |
| Alloa Athletic | 2 – 0 | Whitehill Welfare |
Third round
edit| Home team | Score | Away team |
|---|---|---|
| Albion Rovers | 1 – 2 | Partick Thistle |
| Arbroath | 1 – 1 | Motherwell |
| Celtic | 1 – 3 | Inverness CT |
| Clyde | 3 – 1 | Raith Rovers |
| Clydebank | 1 – 0 | Stirling Albion |
| Dundee | 0 – 0 | Ayr United |
| Dundee United | 4 – 1 | Airdrieonians |
| Falkirk | 3 – 1 | Peterhead |
| Greenock Morton | 1 – 1 | Brechin City |
| Hearts | 3 – 2 | Stenhousemuir |
| Hibernian | 4 – 1 | Dunfermline Athletic |
| Kilmarnock | 0 – 0 | Alloa Athletic |
| Queen of the South | 0 – 7 | Livingston |
| St Johnstone | 0 – 2 | Rangers |
| St Mirren | 1 – 1 | Aberdeen |
| Stranraer | 1 – 2 | Berwick Rangers |
Replays
edit| Home team | Score | Away team |
|---|---|---|
| Aberdeen | 2 – 0 | St Mirren |
| Alloa Athletic | 1 – 0 | Kilmarnock |
| Ayr United | 1 – 1 (7 – 6 pen.) |
Dundee |
| Motherwell | 2 – 0 | Arbroath |
| Brechin City | 0 – 0 (3 – 4 pen.) |
Greenock Morton |
Fourth round
edit| Home team | Score | Away team |
|---|---|---|
| Alloa Athletic | 2 – 2 | Dundee United |
| Berwick Rangers | 0 – 0 | Falkirk |
| Clyde | 0 – 2 | Hearts |
| Hibernian | 1 – 1 | Clydebank |
| Greenock Morton | 0 – 1 | Rangers |
| Inverness CT | 1 – 1 | Aberdeen |
| Motherwell | 3 – 4 | Ayr United |
| Partick Thistle | 2 – 1 | Livingston |
Replays
edit| Home team | Score | Away team |
|---|---|---|
| Aberdeen | 1 – 0 | Inverness CT |
| Clydebank | 0 – 3 | Hibernian |
| Falkirk | 3 – 0 | Berwick Rangers |
| Dundee United | 4 – 0 | Alloa Athletic |
Quarter-finals
edit| Home team | Score | Away team |
|---|---|---|
| Dundee United | 0 – 1 | Aberdeen |
| Rangers | 4 – 1 | Hearts |
| Ayr United | 2 – 0 | Partick Thistle |
| Hibernian | 3 – 1 | Falkirk |
Semi-finals
edit| Ayr United | 0–7 | Rangers |
|---|---|---|
Rozental  18', 89'Kanchelskis 27'Wallace 41'Dodds 66', 72', 86' |
Final
editLargest Wins
editA list of the largest wins from the competition.
| Score | Home Team | Away Team | Stage |
|---|---|---|---|
| 0-7 | Queen of the South | Livingston | Third Round |
| Ayr United | Rangers | Semi Final | |
| 1-7 | Threave Rovers | Stenhousemuir | First Round |
| 1-5 | Dalbeattie Star | Albion Rovers | Second Round (Replay) |
| 4-0 | Dundee United | Alloa Athletic | Fourth Round |
| 0-4 | Aberdeen | Rangers | Final |
