During the 1938–39 season Hearts competed in the Scottish First Division, the Scottish Cup and the East of Scotland Shield.
| 1938–39 season | |
|---|---|
| Manager |  Frank Moss |
| Stadium | Tynecastle Park |
| Scottish First Division | 4th |
| Scottish Cup | Round 3 |
| Top goalscorer | League:  All: |
Fixtures
editFriendlies
edit| 1 August 1938 Practice Match | Hearts | 6–2 | Heart of Midlothian "A" | Tynecastle Park |
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| 5 August 1938 Practice Match | Hearts | 5–2 | Heart of Midlothian "A" | Tynecastle Park |
| |
| 25 March 1939 Friendly | Middlesbrough | 1–4 | Hearts | Ayresome Park |
| |
Wilson Cup
edit| 17 August 1938 Final | Hearts | 2–0 | Hibernian | Tynecastle Park |
| |
East of Scotland Shield
edit| 7 September 1938 Semi-Final | Hearts | 5–3 | Leith Athletic | Tynecastle Park |
| 15 April 1939 Final | Hearts | 1–3 | Hibernian | Tynecastle Park |
Rosebery Charity Cup
edit| 3 May 1939 Semi-Final | Hearts | 5–2 | St Bernard's | Tynecastle Park |
| |
| 13 May 1939 Final | Hearts | 0–2 | Leith Athletic | Tynecastle Park |
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Scottish Cup
edit| 21 January 1939 Scottish Cup R1 | Hearts | 14–2 | Penicuik Athletic | Tynecastle Park |
| Attendance: 12,620 |
| 4 February 1939 Scottish Cup R2 | Hearts | 14–1 | Elgin City | Tynecastle Park |
| Attendance: 7,857 |
| 18 February 1939 Scottish Cup R3 | Hearts | 2–2 | Celtic | Tynecastle Park |
| Attendance: 50,498 |
| 22 February 1939 Scottish Cup R3 Replay | Celtic | 2–1 | Hearts | Celtic Park |
| Attendance: 80,840 |
Scottish First Division
edit| 13 August 1938 Scottish First Division | Third Lanark | 1–4 | Hearts | Cathkin Park |
| Attendance: 18,000 |
| 20 August 1939 Scottish First Division | Hearts | 6–2 | Falkirk | Tynecastle Park |
| Attendance: 32,070 |
| 24 August 1939 Scottish First Division | Hearts | 4–1 | Third Lanark | Tynecastle Park |
| Attendance: 20,137 |
| 27 August 1939 Scottish First Division | Partick Thistle | 3–1 | Hearts | Firhill Park |
| Attendance: 20,000 |
| 3 September 1938 Scottish First Division | Hearts | 1–5 | Celtic | Tynecastle Park |
| Attendance: 49,905 |
| 10 September 1938 Scottish First Division | Hibernian | 4–0 | Hearts | Easter Road |
| Attendance: 30,000 |
| 13 September 1938 Scottish First Division | Falkirk | 0–1 | Hearts | Brockville Park |
| Attendance: 8,000 |
| 17 September 1938 Scottish First Division | Hearts | 4–0 | Motherwell | Tynecastle Park |
| Attendance: 17,181 |
| 24 September 1938 Scottish First Division | Ayr United | 3–1 | Hearts | Somerset Park |
| Attendance: 9,000 |
| 1 October 1938 Scottish First Division | Hearts | 5–2 | St Mirren | Tynecastle Park |
| Attendance: 11,687 |
| 8 October 1938 Scottish First Division | St Johnstone | 1–7 | Hearts | Muirton Park |
| Attendance: 6,000 |
| 15 October 1938 Scottish First Division | Hearts | 1–1 | Arbroath | Tynecastle Park |
| Attendance: 14,7333 |
| 22 October 1938 Scottish First Division | Hearts | 5–2 | Aberdeen | Tynecastle Park |
| Attendance: 19,907 |
| 29 October 1938 Scottish First Division | Queen's Park | 4–1 | Hearts | Hampden Park |
| Attendance: 11,487 |
| 5 November 1938 Scottish First Division | Queen of the South | 0–1 | Hearts | Palmerston Park |
| Attendance: 7,000 |
| 12 November 1938 Scottish First Division | Hearts | 1–3 | Rangers | Tynecastle Park |
| Attendance: 38,592 |
| 19 November 1938 Scottish First Division | Albion Rovers | 0–1 | Hearts | Cliftonhill |
| Attendance: 6,000 |
| 26 November 1938 Scottish First Division | Raith Rovers | 1–2 | Hearts | Stark's Park |
| Attendance: 12,000 |
| 3 December 1938 Scottish First Division | Hearts | 2–1 | Kilmarnock | Tynecastle Park |
| Attendance: 16,337 |
| 10 December 1939 Scottish First Division | Clyde | 2–6 | Hearts | Shawfield Stadium |
| Attendance: 12,000 |
| 17 December 1938 Scottish First Division | Hearts | 2–3 | Hamilton Academical | Tynecastle Park |
| Attendance: 20,409 |
| 24 December 1938 Scottish First Division | Hearts | 5–0 | Partick Thistle | Tynecastle Park |
| Attendance: 9,904 |
| 31 December 1938 Scottish First Division | Celtic | 2–2 | Hearts | Celtic Park |
| Attendance: 50,446 |
| 2 January 1939 Scottish First Division | Hearts | 0–1 | Hibernian | Tynecastle Park |
| Attendance: 45,061 |
| 3 January 1939 Scottish First Division | Arbroath | 1–1 | Hearts | Gayfield Park |
| Attendance: 6,000 |
| 11 January 1939 Scottish First Division | Hearts | 2–0 | Ayr United | Tynecastle Park |
| Attendance: 6,400 |
| 24 January 1939 Scottish First Division | St Mirren | 2–1 | Hearts | St Mirren Park, Love Street |
| Attendance: 5,000 |
| 28 January 1939 Scottish First Division | Hearts | 8–2 | St Johnstone | Tynecastle Park |
| Attendance: 9,740 |
| 11 February 1939 Scottish First Division | Motherwell | 4–2 | Hearts | Fir Park |
| Attendance: 12,000 |
| 25 February 1939 Scottish First Division | Aberdeen | 4–3 | Hearts | Pittodrie Park |
| Attendance: 19,000 |
| 4 March 1939 Scottish First Division | Hearts | 8–3 | Queen's Park | Tynecastle Park |
| Attendance: 8,245 |
| 11 March 1939 Scottish First Division | Hearts | 1–2 | Queen of the South | Tynecastle Park |
| Attendance: 7,491 |
| 18 March 1939 Scottish First Division | Rangers | 1–1 | Hearts | Ibrox Park |
| Attendance: 40,000 |
| 29 March 1939 Scottish First Division | Hearts | 2–0 | Albion Rovers | Tynecastle Park |
| Attendance: 7,091 |
| 1 April 1939 Scottish First Division | Hearts | 2–1 | Raith Rovers | Tynecastle Park |
| Attendance: 9,918 |
| 8 April 1939 Scottish First Division | Kilmarnock | 4–1 | Hearts | Rugby Park |
| Attendance: 6,000 |
| 26 April 1939 Scottish First Division | Hearts | 2–0 | Clyde | Tynecastle Park |
| Attendance: 7,091 |
| 29 April 1939 Scottish First Division | Hamilton Academical | 4–1 | Hearts | Douglas Park |
| Attendance: 2,000 |