Swalwell, County Durham born inside forward Jimmy Armstrong began his football career in north east football with Spen Black & White joining First Division Chelsea in January 1922. He made his Football League debut at Tottenham Hotspur in December 1922, scoring in a 3-1 defeat, and he found the net a further 7 times in 15 more appearances in his debut season. He made 13 appearances in his second season, scoring twice, as Chelsea were relegated to the Second Division in 1924, however he only made two more appearances in the next three and a half years until he joined Tottenham Hotspur in December 1927.
Despite four goals in 15 appearances he couldn’t help Spurs avoid the drop at the end of the 1927-28 season and he spent two further seasons on the fringe at White Hart Lane leaving to join Luton Town in the summer of 1930 after 5 goals in 33 appearances. He didn’t complete a season at Kenilworth Road, scoring twice in 11 appearances, before he joined Bristol Rovers in March 1931, where he scored twice in 9 further appearances before leaving the professional game at the end of the 1930-31 season.