The 1995–96 Scottish Challenge Cup was the sixth season of the competition, competed for by the 30 member clubs of the Scottish Football League. The previous champions were Airdrieonians, who defeated Dundee 3–2 after extra in the 1994 final. The final was played on 5 November 1995, between Stenhousemuir and Dundee United at McDiarmid Park in Perth. Stenhousemuir won 5–4 penalties after a 0–0 draw after extra time, to win the tournament for the first time.