Matches: 1965 – 1966 | Match Pictures: 1965-66 | League Cup |
Celtic were in Group 1
| Dundee Utd |
2 – 1 | Celtic | Link |
| Motherwell |
1 – 0 |
Dundee | |
| Celtic |
1 – 0 | Motherwell | Link |
| Dundee |
0 – 0 |
Dundee Utd | |
| Celtic |
0 – 2 |
Dundee | Link |
| Dundee Utd |
4 – 1 | Motherwell | |
| Celtic |
3 – 0 | Dundee Utd | Link |
| Dundee |
1 – 2 |
Motherwell | |
| Dundee Utd |
1 – 3 |
Dundee | |
| Motherwell | 2 – 3 | Celtic | Link |
| Dundee | 1 – 3 | Celtic | Link |
| Motherwell |
3 – 2 |
Dundee Utd |
Celtic were joined by the following teams in the Quarter Finals
| Group | Team | W | D | L | F | A | GAv | Pts |
| 1 | Celtic | 4 | 0 | 2 | 11 | 7 | 1.57 | 8 |
| 2 | Rangers | 4 | 0 | 2 | 13 | 7 | 1.86 | 8 |
| 3 | Kilmarnock | 5 | 0 | 1 | 11 | 3 | 3.67 | 10 |
| 4 | Hibernian | 5 | 0 | 1 | 15 | 6 | 2.50 | 10 |
| 5 | Third Lanark | 3 | 2 | 1 | 13 | 10 | 1.30 | 8 |
| 6 | Raith Rovers | 4 | 2 | 0 | 15 | 7 | 2.14 | 10 |
| 7 | Airdrie | 5 | 0 | 1 | 22 | 13 | 1.69 | 10 |
| 8 | Alloa | 4 | 0 | 2 | 10 | 10 | 1.00 | 8 |
| 9 | Ayr Utd | 4 | 0 | 0 | 14 | 3 | 4.67 | 8 |
* Ayr Utd qualified from the expanded Group of 5 teams
Supplementary Round:
Third Lanark 1-2 Ayr Utd
Ayr Utd 1-2 Third Lanark
Aggregate:
Ayr Utd 3-1 Third Lanark
Quarter Finals
| Team | Agg. | Team | 1st Leg | 2nd Leg | Playoff |
| Airdrie | 1-9 | Rangers |
1-5 | 0-4 | |
| Alloa |
2-13 | Hibernian |
0-2 | 2-11 | |
| Kilmarnock | 4-2 | Ayr Utd |
2-0 | 2-2 | |
| Raith Rovers |
1-12 | Celtic | 1-8 | 0-4 |
Semi Finals:
| Team | Team | |
| Celtic | 2-2 | Hibernian |
| Rangers |
6-4 | Kilmarnock |
Semi-Final Replay:
Celtic 4 – 0 Hibernian
Final:
Played at Hampden Park, 25th October, 1965.Rangers 1 – 2 Celtic
Winners League Cup 1965-66 Celtic