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There was little innovation in the way of kit design during the Twenties and early Thirties. The club disposed of a collar on the team shirt and again opted for the crew neck and laces. The new shirt style coincided with the arrival in the colours of Glentoran's goal scoring phenomenon Fred Roberts. The iconic Roberts first played in this shirt during the 1928/29 season when he signed for the East Belfast side from Broadway United. Two seasons later he would set the club's all time scoring record bagging 96 goals in just over 40 appearances. The Glens would win the league in '31, the Irish Cup in '32 and again in '33, the season in which Glentoran officials dropped the bombshell of announcing that they would be handing Roberts a free transfer due to a poor run in the league. 332 goals in 221 appearance over a 5 year career in the red, green and black would not be enough to save the giant hero.

Poor quality archive photographs from the Twenties and Thirties meant that pictures had to be lightened considerably to ascertain shirt patterns. Many Glentoran photographs of the time appeared to show rather austere dark shirts however when they were lightened it turned out that they had fairly modern styling. This shirt was worn throughout several seasons and seems to have had more usage at the start of the Thirties. This could well have been the jersey most used by Fred Roberts during the epic 1930/31 season. The league was won at a trot and Roberts broke all the rules with his goal scoring heroics. The shirt would also be worn by Oval legends such as John Geary and Peter Doherty. A Leeman, a Mathieson, a Morgan, a Brown, a Ward, a Bowers, a Morrison, a Bruce and a Walker would all play for
the Glens wearing this kit.