Gary’s career began in the youth team at Ross County. He had trials at Liverpool before moving to the Merseyside club in March 2007, still just 17 years old. He never made it to the Liverpool first team, spending his time there in the youth and reserve sides. Gary also suffered injuries which curtailed his progress and after two years at Anfield he was released.

He spent some time with Fulham before he joined Airdrie United in January 2011 on a short term deal and he made over twenty appearances for them. He made a good impression there and was closely monitored by United and after trials with Dundee United he signed a two year contract in July 2011.

After making his debut in the Europa League tie against Slask Wroclaw, Gary had a slow start to the 2011-12 season, only making appearances from the bench for the first few months. He scored his first goal for the club in the 3-3 draw with St Johnstone at McDiarmid Park, and scored again in the 4-1 win in Dunfermline at the end of October. He gained his first starting place at Ibrox at the beginning of November, and he went from strength to strength, proving a fans favourite with his exciting wing play and creativity, setting up 11 goals in the second half of the season. He scored against his former club in the 6-2 win over Airdrie United in the Scottish Cup, and added further goals against Hibs at Easter Road and Hearts at Tannadice.

Gary’s impact on the first team helped the recovery from a poor start to the season, and helped lift the team up to 4th in the SPL. His recognition went further afield than just Tannadice, with a call up to the Scotland U21 squad in February, winning his first cap against the Netherlands. He was overwhelmingly voted as United’s Young Player of the Year, and narrowly missed out on winning the PFA Scotland’s Young Player of the Year award.