1999–2000 Inverness Caledonian Thistle F.C. season

Inverness Caledonian Thistle F.C. in their sixth season in the Scottish Football League competed in the Scottish First Division, Scottish League Cup, the Scottish Challenge Cup, the Scottish Challenge Cup where they made their first major final against Second Division team Alloa Athletic where they lost on a penalty shoot-out after a 4–4 draw and Scottish Cup where they famously beat Scottish Premier League team Celtic 3–1 in the 3rd Round in season 1999–2000.