In 1920, Irving joined Scottish Football League side Dundee where he quickly established himself in the first team. He spent six years with the club, making over 150 appearances in all competitions, despite suffering persistent knee injuries for several years. He helped the club to two top four finishes and reach the 1925 Scottish Cup Final where they were defeated by Celtic. He joined Football League First Division side Cardiff City in 1926 in a swap deal with Joe Cassidy. In his first year with the club, he helped them win both the FA Cup, becoming the only team from outside England to win the competition, and the Welsh Cup. He also won the 1927 FA Charity Shield the following year, but fell out of favour midway through the 1927–28 season.