Jamie started his youth football at Coupar Angus Boys Club, and arrived at Tannadice at the age of 12 via city rivals Dundee. After attending Blairgowrie High School he signed his first professional form for United in 2014.
With left back options limited in the first team during the start of the 2015-16 season, Jamie made his first team debut under Jackie McNamara in the Scottish League Cup towards the end of the manager’s tenure while also featuring regularly for the Development squad. He was an unused substitute for Mixu Paatelainen’s first few games in charge, and after signing a two year contract extension in January 2016, he joined Brechin City on loan until the end of the season. He made six appearances in League One, scoring twice, before returning to United for a place on the bench for the Inverness game at the business end of the season.