Kyle is a Scottish winger who came through the youth system at St Mirren making his first team debut in February 2013. Kyle signed for Derby County in January 2017 for an undisclosed fee. He returned to St Mirren on loan for the second half of the 2018-19 season, helping the side to stay in the Scottish Premiership. In August 2019, McCallister left Derby and signed a long-term contract with St Mirren.
Having played for the U17 side in 2015-16 Kyle made his debut for Scotland U21s in March 2019 against Sweden before being involved in the UEFA European U21 Championship Qualifying matches.