During the 1939–40 season and after the outbreak of World War II which suspended the usual Scottish Football League, Hearts competed in the Emergency League Eastern Division, the Emergency Cup and the East of Scotland Shield.
Fixtures
Friendlies
| 2 August 1939 Trail | Hearts | 7–0 | Hearts "A" | Tynecastle Park |
| 7 August 1939 Trail | Hearts | 5–0 | Hearts "A" | Tynecastle Park |
| 23 September 1939 Friendly | Hearts | 2–4 | Hibernian | Tynecastle Park |
| 7 October 1939 Friendly | Hearts | 4–2 | Partick Thistle | Tynecastle Park |
| 14 October 1939 Friendly | Hearts | 5–2 | Celtic | Tynecastle Park |
Wilson Cup
| 16 August 1939 Final | Hibernian | 0–2 | Hearts | Easter Road |
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East of Scotland Shield
| 30 August 1939 Semi-Final | Hearts | 7–0 | Leith Athletic | Tynecastle Park |
| 15 May 1940 Final | Hibernian | 3–2 | Hearts | Easter Road |
Rosebery Charity Cup
| 22 May 1940 Semi-Final | Hearts | 3–1 | Leith Athletic | Tynecastle Park |
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| 1 June 1940 Final | Hearts | 2–5 | Hibernian | Tynecastle Park |
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Scottish First Division (abandoned)
| 12 August 1939 Scottish First Division | Hearts | 1–1 | Partick Thistle | Tynecastle Park |
| 19 August 1939 Scottish First Division | Celtic | 2–0 | Hearts | Celtic Park |
| 22 August 1939 Scottish First Division | Partick Thistle | 1–2 | Hearts | Tynecastle Park |
| 26 August 1939 Scottish First Division | Hearts | 6–2 | Ayr United | Tynecastle Park |
| 2 September 1939 Scottish First Division | Motherwell | 2–4 | Hearts | Fir Park |
Emergency Cup
| 24 February 1940 Emergency Cup R1 1st Leg | St Johnstone | 2–1 | Hearts | Muirton Park |
| Attendance: 4,300 |
| 2 March 1940 Emergency Cup R1 2nd Leg | Hearts | 5–0 | St Johnstone | Tynecastle Park |
| Attendance: 7,974 |
| 9 March 1940 Emergency Cup R2 | Hearts | 2–1 | Raith Rovers | Tynecastle Park |
| Attendance: 9,951 |
| 23 March 1940 Emergency Cup Quarter-Final 1st Leg | Airdrieonians | 0–0 | Hearts | Broomfield Park |
| Attendance: 14,000 |
| 27 March 1940 Emergency Cup Quarter-Final 2nd Leg | Hearts | 2–2 | Airdrieonians | Tynecastle Park |
| Attendance: 19,949 |
| 1 April 1940 Emergency Cup Quarter-Final Replay | Hearts | 3–4 | Airdrieonians | Tynecastle Park |
| Attendance: 20,000 |
Emergency League Eastern Division
| 21 October 1939 Emergency League Eastern Division | Hearts | 2–3 | Falkirk | Tynecastle Park |
| Attendance: 4,500 |
| 28 October 1939 Emergency League Eastern Division | Raith Rovers | 1–5 | Hearts | Stark's Park |
| 4 November 1939 Emergency League Eastern Division | Hearts | 2–2 | St Bernard's | Tynecastle Park |
| 11 November 1939 Emergency League Eastern Division | Alloa Athletic | 2–3 | Hearts | Recreation Park |
| 18 November 1939 Emergency League Eastern Division | Hearts | 9–2 | Dundee United | Tynecastle Park |
| Attendance: 3,715 |
| 25 November 1939 Emergency League Eastern Division | Dunfermline Athletic | 5–2 | Hearts | East End Park |
| 2 December 1939 Emergency League Eastern Division | Hearts | 6–3 | East Fife | Tynecastle Park |
| 9 December 1939 Emergency League Eastern Division | Dundee | 4–6 | Hearts | Dens Park |
| 16 December 1939 Emergency League Eastern Division | Hearts | 3–2 | Aberdeen | Tynecastle Park |
| Attendance: 4,000 |
| 23 December 1939 Emergency League Eastern Division | Cowdenbeath | 1–1 | Hearts | Central Park |
| 30 December 1939 Emergency League Eastern Division | Hearts | 8–2 | Stenhousemuir | Tynecastle Park |
| 1 January 1940 Emergency League Eastern Division | Hibernian | 4–6 | Hearts | Easter Road |
| Attendance: 14,000 |
| 2 January 1940 Emergency League Eastern Division | Hearts | 7–2 | Arbroath | Tynecastle Park |
| 6 January 1940 Emergency League Eastern Division | King's Park | 2–2 | Hearts | Forthbank Park |
| 13 January 1940 Emergency League Eastern Division | Hearts | 3–0 | St Johnstone | Tynecastle Park |
| 10 February 1940 Emergency League Eastern Division | Hearts | 7–2 | Alloa Athletic | Tynecastle Park |
| Attendance: 5,000 |
| 17 February 1940 Emergency League Eastern Division | Dundee United | 3–2 | Hearts | Tannadice Park |
| Attendance: 3,000 |
| 16 March 1940 Emergency League Eastern Division | Aberdeen | 3–0 | Hearts | Pittodrie Park |
| 30 March 1940 Emergency League Eastern Division | Stenhousemuir | 1–0 | Hearts | Ochilview Park |
| 3 April 1940 Emergency League Eastern Division | Falkirk | 7–1 | Hearts | Brockville Park |
| Attendance: 5,000 |
| 6 April 1940 Emergency League Eastern Division | Hearts | 4–0 | Hibernian | Tynecastle Park |
| 10 April 1940 Emergency League Eastern Division | Hearts | 4–3 | Raith Rovers | Tynecastle Park |
| 13 April 1940 Emergency League Eastern Division | Arbroath | 2–2 | Hearts | Gayfield Park |
| 15 April 1940 Emergency League Eastern Division | St Bernard's | 0–2 | Hearts | Tynecastle Park |
| 20 April 1940 Emergency League Eastern Division | Hearts | 7–2 | King's Park | Tynecastle Park |
| 27 April 1940 Emergency League Eastern Division | St Johnstone | 2–2 | Hearts | Muirton Park |
| 4 May 1940 Emergency League Eastern Division | East Fife | 1–2 | Hearts | Bayview Park |
| 11 May 1940 Emergency League Eastern Division | Hearts | 2–3 | Dundee | Tynecastle Park |
| 25 May 1940 Emergency League Eastern Division | Hearts | 2–0 | Dunfermline Athletic | Tynecastle Park |
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