Berwick Rangers 1-0 Rangers, 28 January 1967. Rangers would go on to contest a European final that year but they could not get past Second Division Berwick Rangers, and goalkeeper Jock Wallace, in the first round of the Scottish Cup.
Great Cup Shocks - Berwick Rangers 1-0 Rangers 1967
Stenhousemuir 2-0 Aberdeen, 18 February 1995. Aberdeen have had some miserable experiences in the cups in recent years, but this fourth-round defeat by Second Division Stenhousemuir was particularly painful for the Dons.
Great Cup Shocks - Stenhousemuir 2-0 Aberdeen 1995
Celtic 1-3 Inverness Caledonian Thistle, 8 February 2000. This third-round defeat by First Division Inverness, said to be Celtic's worst in 30 years, signalled the end for manager John Barnes.
Great Cup Shocks - Celtic 1-3 Inverness Caledonian Thistle
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