1899–1900 Heart of Midlothian F.C. season
During the 1899–1900 season Hearts competed in the
Scottish First Division, the Scottish Cup and the East of Scotland Shield
.
Fixtures
East of Scotland Shield
| 5 May 1900 East of Scotland Shield Final | Hibernian | 0–3 | Hearts | Easter Road |
Rosebery Charity Cup
| 24 April 1900 Rosebery Charity Cup SF | St Bernard's | 0–4 | Hearts | Easter Road |
| 19 May 1900 Rosebery Charity Cup Final | Hearts | 3–3 | Hibernian | Tynecastle Park |
| 23 May 1900 Rosebery Charity Cup Final Replay | Hearts | 3–0 | Hibernian | Old Powderhall |
Scottish Cup
| 13 January 1900 Scottish Cup R1 | Hearts | 0–0 | St Mirren | Tynecastle Park |
| Attendance: 6,500 |
| 20 January 1900 Scottish Cup R1 Replay | St Mirren | 0–3 | Hearts | Love Street |
| Attendance: 6,000 |
| 27 January 1900 Scottish Cup R2 | Hearts | 1–1 | Hibernian | Tynecastle Park |
| Attendance: 14,000 |
| 3 February 1900 Scottish Cup R2 Replay | Hibernian | 1–2 | Hearts | Easter Road |
| Attendance: 12,500 |
| 10 February 1900 Scottish Cup R3 | Third Lanark | 1–2 | Hearts | Cathkin Park |
| Attendance: 3,000 |
| 10 March 1900 Scottish Cup SF | Queen's Park | 2–1 | Hearts | Hampden Park |
| Attendance: 16,000 |
East of Scotland League
| 15 August 1900 East of Scotland League | Hearts | 1–3 | Leith Athletic | Tynecastle Park |
| 15 August 1900 East of Scotland League | Hearts | 1–3 | Leith Athletic | Tynecastle Park |
| 6 January 1900 East of Scotland League | Hearts | 7–0 | Raith Rovers | Tynecastle Park |
| 24 March 1900 East of Scotland League | Hearts | 2–1 | Dundee | Tynecastle Park |
| 9 April 1900 East of Scotland League | Dundee | 1–0 | Hearts | Dens Park |
| 14 April 1900 East of Scotland League | Hearts | 0–0 | Leith Athletic | Tynecastle Park |
| 30 April 1900 East of Scotland League | St Bernard's | 3–1 | Hearts | Old Logie Green |
| 12 May 1900 East of Scotland League | Hibernian | 0–0 | Hearts | Easter Road |
Inter City League
| 30 December 1899 Ibrox Park |
| 1 January 1900 Inter City Football League | Hearts | 3–3 | Hibernian | Tynecastle Park |
| 17 February 1900 Inter City Football League | Queen's Park | 1–0 | Hearts | Hampden Park |
| 3 March 1900 Inter City Football League | Hearts | 1–3 | Third Lanark | Tynecastle Park |
| 31 March 1900 Cathkin Park |
| 7 April 1900 Inter City Football League | Hearts | 4–1 | Rangers | Tynecastle Park |
| 16 April 1900 Inter City Football League | Hibernian | 1–1 | Hearts | Easter Road |
| 21 April 1900 Inter City Football League | Hearts | 3–2 | Celtic | Tynecastle Park |
| 28 April 1900 Inter City Football League | Hearts | 4–1 | Queen's Park | Tynecastle Park |
| 7 May 1900 Inter City Football League | Celtic | 5–0 | Hearts | Celtic Park |
Scottish First Division
| 2 September 1899 Ibrox Park | ||||
| Attendance: 20,000 |
| 9 September 1899 Scottish First Division | St Bernard's | 2–4 | Hearts | New Logie Green |
| Attendance: 6,000 |
| 16 September 1899 Scottish First Division | Hearts | 3–0 | Celtic | Tynecastle Park |
| Attendance: 6,500 |
| 18 September 1899 Scottish First Division | Hearts | 1–1 | Rangers | Tynecastle Park |
| Attendance: 15,500 |
| 23 September 1899 Scottish First Division | Hearts | 1–0 | Kilmarnock | Tynecastle Park |
| Attendance: 5,000 |
| 30 September 1899 Scottish First Division | Celtic | 0–2 | Hearts | Celtic Park |
| Attendance: 10,000 |
| 7 October 1899 Scottish First Division | Hearts | 2–0 | Third Lanark | Tynecastle Park |
| Attendance: 4,500 |
| 14 October 1899 Scottish First Division | Hearts | 5–0 | St Bernard's | Tynecastle Park |
| Attendance: 4,200 |
| 21 October 1899 Scottish First Division | Clyde | 1–2 | Hearts | Shawfield Stadium |
| Attendance: 4,000 |
| 28 October 1899 Scottish First Division | Hibernian | 1–0 | Hearts | Easter Road |
| Attendance: 9,000 |
| 4 November 1899 Scottish First Division | Hearts | 3–2 | Celtic | Tynecastle Park |
| Attendance: 10,000 |
| 11 November 1899 Scottish First Division | Hearts | 4–1 | Dundee | Tynecastle Park |
| Attendance: 2,500 |
| 18 November 1899 Scottish First Division | St Mirren | 2–2 | Hearts | St Mirren Park, Love Street |
| Attendance: 3,000 |
| 25 November 1899 Scottish First Division | Hearts | 1–3 | Hibernian | Tynecastle Park |
| Attendance: 7,500 |
| 9 December 1899 Scottish First Division | Hearts | 4–1 | Clyde | Tynecastle Park |
| Attendance: 2,000 |
| 23 December 1899 Cathkin Park | ||||
| Attendance: 3,000 |
| 17 March 1900 Scottish First Division | Kilmarnock | 2–1 | Hearts | Rugby Park |
| Attendance: 4,500 |