Rutherglen, Lanarkshire born inside left Jimmy Howieson had been serving in the Royal Navy before joining hometown junior club Rutherglen Glencairn in 1921. In November 1921 he moved to Airdrieonians for £5, and from there transferred to St Johnstone in May 1924. During the season, Howieson played most of St Johnstone’s League games, but went on loan to St Mirren in February 1925, making 4 appearances for The Buddies in a two month spell. At the end of the season, he moved to Dundee United where he scored 5 goals in 10 appearances between August and October 1925, when Dundee United sold Howieson to St Mirren for £1,000. He won the 1926 Scottish Cup with St Mirren, scoring the winning goal as they beat Celtic 2-0 in the Final. On 26th February 1927, Howieson earned his lone cap for Scotland in 2-0 victory over Ireland in Belfast.
In March 1927, St Mirren sent him south to Second Division Hull City broke their club record transfer fee in a £3,200 transfer after Howieson’s 17 goals in 51 appearances in his second spell at Love Street, Howieson making his Football League debut against Grimsby Town the same month. He scored 7 goals in 40 appearances for The Tigers before, a season later, he left the British Isles to join the New Bedford Whalers for the 1928-29 American Soccer League season.
That season saw the outbreak of the “Soccer War” between the ASL and the United States Football Association over control of the sport. As part of that dispute, the USFA and FIFA declared the ASL and outlaw league and created a competing league, the Eastern Professional Soccer League. Although the Whalers remained in the ASL for most of the season, it moved to the EPSL in the spring of 1929. Howieson played thirty-five games, scoring nine goals in the ASL, then another eight games, scoring eight goals, in the EPSL. With four games left in the season, the Whalers sent Howieson to the New York Giants for four games.
At the end of the season, Howieson returned to Hull City for the 1929-30 season, where he scored 7 goals in a further 34 appearances but couldn’t prevent their relegation, and he played in their famous FA Cup run that season when they were beaten in the 1930 FA Cup semi final by eventual winners Arsenal in a replay at Villa Park.
In June 1930, Hull transferred him to Irish League club Shelbourne. He then played for Clyde, joining them in September 1932, moving to Alloa Athletic in the summer of 1934 for a brief spell before a return to Ireland, joining Glenavon later in 1934 and then playing for Belfast Celtic before retiring in 1936.