Career
In a twenty-year playing career, he made over 100 appearances for both Dundee United and Street Johnstone. He also played for Airdrieonians, Greenock Morton, Ayr United, Stirling Albion and Brechin City. He made three appearances for the Scotland under-21 team in 1990.
After retiring from playing, Connolly was assistant manager of Albion Rovers and Alloa Athletic, and was caretaker manager of Alloa on two occasions in 2015.
Connolly started his career with Dundee United. He spent ten years at Tannadice, after which he joined Airdrie for a short time, before moving to Street Johnstone in 1998.
Connolly spent six years with the Saints, including short loan spells at Morton and Ayr United. Despite being sent out on loan, Connolly agreed a new three-year contract in May 2001, amidst interest from former manager and Plymouth Argyle manager Paul Sturrock.
Connolly missed the final year of his contract due to a cruciate ligament injury, and upon leaving McDiarmid Park in 2004, returned to Ayr, where he spent a season before playing the following season with Stirling Albion.
Disallowed goal
Connolly was involved in one of Scottish football"s more bizarre moments when he was denied a hat-trick during his time at Dundee United, when referee Les Mottram failed to notice his shot had come back from the back stanchion in a February 1993 match against Partick Thistle. Mottram went on to referee in the 1994 World Cup the following year. This resulted in the previously widely used stanchions which the ball had rebounded off, being removed in a re-design of football goalposts.
Nine months later, he left the club due to work commitments elsewhere, joining Fulham as a scout around November 2009.
On 18 May 2011, Connolly was appointed assistant manager to Paul Hartley at Alloa Athletic. He continued as assistant manager under Barry Smith and was appointed caretaker manager after Smith left the club in March 2015.
Connolly continued to work for Alloa under the management of Danny Lennon and was appointed caretaker when Lennon resigned in December 2015.