The 1876–77 Scottish Cup – officially the Scottish Football Association Challenge Cup – was the fourth season of Scotland's most prestigious football knockout competition. Entries to the competition again increased with a total of 81 clubs involved in the first round draw. This resulted in an earlier start to the competition than in previous seasons with the first matches played on 23 September 1876. The cup was won for the first time by Dunbartonshire club Vale of Leven who defeated Rangers 3–2 in a twice-replayed final. This was the first final which did not involve defending champions Queen's Park who lost 2–1 to Vale of Leven in the quarter-finals and the first time the cup was won by a team from outside Glasgow.

Calendar

Teams

All 81 teams entered the competition in the first round.

First round

Glasgow and District

Renfrewshire district

Dunbartonshire district

Edinburgh district

Ayrshire district

Kilmarnock received a bye to the second round.

Lanarkshire district

Sources:

Second round

Glasgow and District

Dunbartonshire district

Edinburgh district

Lanarkshire district

Renfrewshire district

Ayrshire district

Sources:

Third round

Rangers received a bye to the fourth round.

Fourth round

Sources:

Quarter-finals

Sources:

Semi-final

Rangers received a bye to the final. Sources:

Final

Replay

Second replay