| Scottish Cup | |
| Year: | 1898–99 |
| Country: | Scotland |
| Defending Champions: | Rangers |
| Winners: | Celtic |
| Second: | Rangers |
| Prev Season: | 1897–98 |
| Next Season: | 1899–1900 |
The 1898–99 Scottish Cup was the 26th season of Scotland's most prestigious football knockout competition. The cup was won by Celtic when they beat holders Rangers 2–0 in the final at the second Hampden Park to claim victory in the competition for the second time.
| Round | First match date | Fixtures | width=100 | Clubs | ||
|---|---|---|---|---|---|---|
| align=left | First round | align=left | 14 January 1899 | 16 | 32 → 16 | |
| align=left | Second round | align=left | 11 February 1899 | 8 | 16 → 8 | |
| align=left | Quarter-finals | align=left | 18 February 1899 | 4 | 8 → 4 | |
| align=left | Semi-finals | align=left | 11 March 1899 | 2 | 4 → 2 | |
| align=left | Final | align=left | 22 April 1899 | 1 | 2 → 1 |
| width=140 | Home team | width=80 | Score | width=140 | Away team |
|---|---|---|---|---|---|
| Airdrieonians | 3 – 3 | Arbroath | |||
| Ayr Parkhouse | 3 – 1 | Dundee | |||
| Clyde | 3 – 0 | Wishaw Thistle | |||
| East Stirlingshire | 4 – 1 | Dumbarton | |||
| Bo'ness | 3 – 3 | St Bernard's | |||
| Hibernian | 2 – 1 | Royal Albert | |||
| Forfar Athletic | 4 – 5 | West Calder | |||
| Greenock Morton | 3 – 1 | Annbank | |||
| Orion | 0 – 2 | Kilmarnock | |||
| Partick Thistle | 5 – 0 | Irvine | |||
| Port Glasgow Athletic | 3 – 2 | Renton | |||
| Queen's Park | 4 – 0 | Kilsyth Wanderers | |||
| Rangers | 4 – 1 | Heart of Midlothian | |||
| 6th GRV | 1 – 8 | Celtic | |||
| St Mirren | 7 – 1 | Leith Athletic | |||
| Third Lanark | 4 – 1 | Arthurlie |
| width=140 | Home team | width=80 | Score | width=140 | Away team |
|---|---|---|---|---|---|
| Arbroath | 3 – 2 | Airdrieonians | |||
| St Bernard's | 4 – 2 | Bo'ness |
| width=140 | Home team | width=80 | Score | width=140 | Away team |
|---|---|---|---|---|---|
| Ayr Parkhouse | 1 – 4 | Rangers | |||
| Celtic | 3 – 0 | St Bernard's | |||
| Clyde | 3 – 1 | Arbroath | |||
| East Stirlingshire | 1 – 1 | Kilmarnock | |||
| Partick Thistle | 2 – 2 | Greenock Morton | |||
| 3 – 1 | West Calder | ||||
| Queen's Park | 5 – 1 | Hibernian | |||
| St Mirren | 2 – 1 | Third Lanark |
| width=140 | Home team | width=80 | Score | width=140 | Away team |
|---|---|---|---|---|---|
| Kilmarnock | 0 – 0 | East Stirlingshire | |||
| Greenock Morton | 1 – 2 | Partick Thistle |
| width=140 | Home team | width=80 | Score | width=140 | Away team |
|---|---|---|---|---|---|
| Kilmarnock | 4 – 2 | East Stirlingshire |
| width=140 | Home team | width=80 | Score | width=140 | Away team |
|---|---|---|---|---|---|
| Kilmarnock | 1 – 2 | St Mirren | |||
| Queen's Park | 2 – 4 | Celtic * | |||
| Port Glasgow Athletic | 7 – 3 | Partick Thistle | |||
| Rangers | 4 – 0 | Clyde |
| width=140 | Home team | width=80 | Score | width=140 | Away team |
|---|---|---|---|---|---|
| Celtic | 2 – 1 | Queen's Park |
| width=140 | Home team | width=80 | Score | width=140 | Away team |
|---|---|---|---|---|---|
| Celtic | 4 – 2 | Port Glasgow Athletic | |||
| St Mirren | 1 – 2 | Rangers |
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