He broke through into the first team during a relegation struggle in the 1994–95 season, and scored goals in the final league fixture and in both legs of the subsequent playoff to maintain his club's top-division status.
Glass played a bit-part role in Newcastle's following two campaigns, making only six league starts out of a possible seventy-six, although he did score the equaliser in a 1–1 home draw with Manchester United in December 2000.
Ironically, after this announcement was made he scored a stunning free-kick in Watford's victory over Burnley in the FA Cup quarter-final.
Despite flashes of his expected pedigree, Glass' first season at Easter Road was also blighted by injury, causing him to miss the 2004 Scottish League Cup Final.
His second season in Edinburgh, however, proved much more successful and his performances under new boss Tony Mowbray helped the club gain a UEFA Cup place by finishing third in the SPL.
Injury to left-back David Murphy in November, however, saw him drafted in as cover and his dependable performances won him his midfield berth back after the new year.
Glass was overlooked for the vacant Hibs captaincy in favour of Gary Caldwell and then Kevin Thomson in 2005 and 2006, perhaps because manager Mowbray no longer saw him to be certain of automatic first-team selection.
Having made only two first-team starts for Hibs during the first half of the 2006–07 season, he was allowed to move to Dunfermline Athletic to gain more regular first team football.
[15] Having left Aberdeen for Newcastle, Glass returned to Pittodrie in October 1998, making his first and only appearance for his country's full side as a substitute in Scotland's 2–1 win over the Faroe Islands.
[20] On 13 January 2012, Glass joined Shamrock Rovers as assistant manager, working for his former Dunfermline boss Stephen Kenny.
[23] On July 27, 2020, Glass was named interim coach of Atlanta United,[24] replacing Frank de Boer, who had departed the club by mutual agreement a few days prior.
[25] Glass returned to his role at Atlanta United 2 after Gabriel Heinze was appointed the full-time coach of the club's first-team in January 2021.