Connachan joined Dunfermline from Dalkeith Thistle in May 1957 and went on to play 172 games for Dunfermline. He helped the club win the Scottish Cup for the first time in 1961 in what was to become known as "Connachan's Cup Final" as he made save after save from the Celtic forwards and he earned two caps for Scotland, against Czechoslovakia in November 1961 and Hungary in May 1962.[3] He also earned selection in the Scottish League representative side.[4]
Connachan joined Middlesbrough in August 1963 for £5,500, returning to Scotland with Falkirk in November 1966.[4] His final port of call was South Africa, where he played for East London Celtic before retiring. He still resided in the African state.[5]
In March 2007 Connachan was inducted into Dunfermline Athletic's Hall of Fame.[5]