1965–66 Heart of Midlothian F.C. season
| 7th | |
| Scottish Cup | Round 3 |
|---|---|
| League Cup | Group Stage |
| Inter-Cities Fairs Cup | Round 3 |
| Top goalscorer | League:  All: |
→ | |
During the 1965–66 season Hearts competed in the
Scottish First Division, the Scottish Cup, the Scottish League Cup, the Inter-Cities Fairs Cup and the East of Scotland Shield
.
Fixtures
Friendlies
| 27 September 1965 Friendly | Hearts | 1–2 | Coleraine | Tynecastle Park |
 |
| 4 October 1965 Friendly | Selkirk | 0–11 | Hearts | Ettrick Park |
|
| 11 October 1965 Friendly | Hearts | 2–1 | Newcastle United | Tynecastle Park |
|
East of Scotland Shield
| 4 May 1966 Final 1st Leg | Hibernian | 1–3 | Hearts | Easter Road |
| 7 May 1966 Final 2nd Leg | Hearts | 4–2 | Hibernian | Tynecastle Park |
Inter-Cities Fairs Cup
| 18 October 1965 Inter-Cities Fairs Cup R2 1st Leg | Hearts | 1–0 | Vålerenga | Tynecastle Park |
|
Attendance: 9,000 |
| 27 October 1965 Inter-Cities Fairs Cup R2 2nd Leg | Vålerenga | 1–3 | Hearts | Ullevaal Stadion |
|
Attendance: 14,625 |
| 12 January 1966 Inter-Cities Fairs Cup R3 1st Leg | Hearts | 3–3 | Real Zaragoza | Tynecastle Park |
|
Attendance: 17,200 |
| 26 January 1966 Inter-Cities Fairs Cup R3 2nd Leg | Real Zaragoza | 2–2 | Hearts | La Romareda |
|
Attendance: 24,230 |
| 2 March 1966 Inter-Cities Fairs Cup R3 Replay | Real Zaragoza | 1–0 | Hearts | La Romareda |
|
Attendance: 25,000 |
League Cup
| 14 August 1965 League Cup Group | Hearts | 4–2 | Rangers | Tynecastle Park |
| Attendance: 32,859 |
| 18 August 1965 League Cup Group | Aberdeen | 1–1 | Hearts | Pittodrie Stadium |
| Attendance: 17,275 |
| 21 August 1965 League Cup Group | Hearts | 1–2 | Clyde | Tynecastle Park |
| Attendance: 12,007 |
| 28 August 1965 League Cup Group | Ibrox Park | |||
| Attendance: 44,472 |
| 1 September 1965 League Cup Group | Hearts | 2–0 | Aberdeen | Tynecastle Park |
| Attendance: 9,981 |
| 4 September 1965 League Cup Group | Clyde | 1–2 | Hearts | Shawfield Stadium |
| Attendance: 2,231 |
Scottish Cup
| 9 February 1966 Scottish Cup R1 | Hearts | 2–1 | Clyde | Tynecastle Park |
| Attendance: 11,875 |
| 21 February 1966 Scottish Cup R2 | Hearts | 2–1 | Hibernian | Tynecastle Park |
| Attendance: 31,244 |
| 5 March 1966 Scottish Cup R3 | Celtic | 3–3 | Hearts | Celtic Park |
| Attendance: 45,965 |
| 9 March 1966 Scottish Cup R3 Replay | Hearts | 1–3 | Celtic | Tynecastle Park |
| Attendance: 72,100 |
Scottish First Division
| 25 August 1965 Scottish First Division | Hearts | 2–0 | Hamilton Academical | Tynecastle Park |
| Attendance: 7,635 |
| 11 September 1965 Scottish First Division | Dunfermline Athletic | 1–1 | Hearts | East End Park |
| Attendance: 11,144 |
| 18 September 1965 Scottish First Division | Hearts | 0–4 | Hibernian | Tynecastle Park |
| Attendance: 22,369 |
| 25 September 1965 Scottish First Division | St Johnstone | 3–2 | Hearts | Muirton Park |
| Attendance: 5,582 |
| 2 October 1965 Scottish First Division | Hearts | 0–0 | Dundee | Tynecastle Park |
| Attendance: 11,605 |
| 9 October 1965 Scottish First Division | Celtic | 5–2 | Hearts | Celtic Park |
| Attendance: 27,115 |
| 16 October 1965 Firhill Park | ||||
| Attendance: 9,653 |
| 23 October 1965 Scottish First Division | Hearts | 5–2 | Motherwell | Tynecastle Park |
| Attendance: 9,507 |
| 30 October 1965 Scottish First Division | Hearts | 1–1 | Hearts | Tynecastle Park |
| Attendance: 10,541 |
| 6 November 1965 Scottish First Division | Dundee United | 2–2 | Hearts | Tannadice Park |
| Attendance: 10,218 |
| 13 November 1965 Scottish First Division | Hearts | 0–2 | Rangers | Tynecastle Park |
| Attendance: 28,697 |
| 20 November 1965 Morton | Tynecastle Park | |||
| Attendance: 9,006 |
| 27 November 1965 Scottish First Division | Falkirk | 0–1 | Hearts | Brockville Park |
| Attendance: 4,132 |
| 11 December 1965 Scottish First Division | Hearts | 4–1 | Clyde | Tynecastle Park |
| Attendance: 7,459 |
| 18 December 1965 Scottish First Division | Stirling Albion | 2–2 | Hearts | Annfield Stadium |
| Attendance: 3,048 |
| 25 December 1965 Scottish First Division | Hearts | 4–0 | St Mirren | Tynecastle Park |
| Attendance: 6,250 |
| 1 January 1966 Scottish First Division | Hibernian | 2–3 | Hearts | Easter Road |
| Attendance: 32,192 |
| 3 January 1966 Scottish First Division | Hearts | 0–0 | Dunfermline Athletic | Tynecastle Park |
| Attendance: 24,579 |
| 8 January 1966 Scottish First Division | Hamilton Academical | 0–1 | Hearts | Douglas Park |
| Attendance: 2,914 |
| 15 January 1966 Scottish First Division | Hearts | 0–0 | St Johnstone | Tynecastle Park |
| Attendance: 6,410 |
| 29 January 1966 Scottish First Division | Hearts | 3–2 | Celtic | Tynecastle Park |
| Attendance: 28,717 |
| 12 February 1966 Scottish First Division | Hearts | 3–1 | Partick Thistle | Tynecastle Park |
| Attendance: 7,659 |
| 26 February 1966 Scottish First Division | Aberdeen | 0–1 | Hearts | Pittodrie Stadium |
| Attendance: 11,934 |
| 12 March 1966 Ibrox Park | ||||
| Attendance: 38,571 |
| 16 March 1966 Scottish First Division | Hearts | 0–1 | Dundee United | Tynecastle Park |
| Attendance: 7,306 |
| 19 March 1966 Cappielow Park | ||||
| Attendance: 5,975 |
| 23 March 1966 Scottish First Division | Motherwell | 4–2 | Hearts | Fir Park |
| Attendance: 2,624 |
| 26 March 1966 Scottish First Division | Hearts | 1–2 | Falkirk | Tynecastle Park |
| Attendance: 5,315 |
| 4 April 1966 Scottish First Division | Kilmarnock | 2–2 | Hearts | Rugby Park |
| Attendance: 5,026 |
| 9 April 1966 Scottish First Division | Hearts | 2–3 | Kilmarnock | Tynecastle Park |
| Attendance: 7,162 |
| 16 April 1966 Scottish First Division | Clyde | 0–1 | Hearts | Shawfield Stadium |
| Attendance: 2,128 |
| 23 April 1966 Scottish First Division | Hearts | 1–1 | Stirling Albion | Tynecastle Park |
| Attendance: 5,465 |
| 30 April 1966 Scottish First Division | St Mirren | 1–1 | Hearts | St Mirren Park, Love Street |
| Attendance: 4,732 |