2003–04 Scottish League Cup
The 2003–04 Scottish League Cup was the 58th staging of the Scotland's second most prestigious football knockout competition, also known for sponsorship reasons as the CIS Insurance Cup.
The competition was won by Livingston, who defeated Hibernian 2–0 in the final.
First round
- Ties played on 2–3 September 2003
- If scores were level at full-time, 30 minutes of extra time and penalties were played.
| Tie No. | Home team | Score | Away team | Report | Attendance |
| 1 | Arbroath | 1–0 | Raith Rovers | 879 | |
| 2 | Ayr | 1–2 | Dumbarton | 1,048 | |
| 3 | Cowdenbeath | 3–0 | Alloa | 288 | |
| 4 | East Fife | 0–2 | Airdrie United | 707 | |
| 5 | East Stirlingshire | 1–2 | Ross County | 208 | |
| 6 | Elgin | 0–4 | Brechin | 486 | |
| 7 | Forfar Athletic | 1–0 | Berwick Rangers | ||
| 8 | Gretna | 1–2 | Peterhead | 385 | |
| 9 | Hamilton Academical | 3–2 | Albion Rovers | 824 | |
| 10 | Inverness CT | 1–2 | Queen's Park | 968 | |
| 11 | Montrose | 2–0 | Stirling Albion | 247 | |
| 12 | St Mirren | 0–2 | St Johnstone | 3,100 | |
| 13 | Stenhousemuir | 1–2 | Queen of the South | 424 | |
| 14 | Greenock Morton | 2–0 | Stranraer | 2,758 |
Second round
- Ties played on 23–24 September 2003
- If scores were level at full-time, 30 minutes of extra time and penalties were played.
| Tie No. | Home team | Score | Away team | Report | Attendance |
| 1 | Aberdeen | 3–1 | Dumbarton | 3,944 | |
| 2 | Arbroath | 3–4 | Falkirk | 923 | |
| 3 | Brechin City | 1–0 | Kilmarnock | 829 | |
| 4 | Clyde | 2–1 | Airdrie United | 1,381 | |
| 5 | Dundee United | 3–1 | Morton | 5,638 | |
| 6 | Forfar Athletic | 3–3 | Motherwell | 1,110 | |
| 7 | Hibernian | 9–0 | Montrose | 5,032 | |
| 8 | Queen's Park | 1–3 | Livingston | 1,011 | |
| 9 | Ross County | 0–3 | Queen of the South | 959 | |
| 10 | St Johnstone | 3–2 | Hamilton | 1,471 | |
| 11 | Dunfermline | 2–0 | Cowdenbeath | 3,582 | |
| 12 | Peterhead | 2–2 | Partick Thistle | 1,350 |
Third round
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Quarter-finals
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