Darlington, County Durham born outside left Tommy Bolland began his football career with Washington United from where he was signed by First Division Sheffield Wednesday in 1907, making his Football League debut at Notts County in January 1908. He scored his only goal for Wednesday in his third match in a 2-0 win over Bury the next month, and played 5 more matches in the run in as Wednesday finished fifth in the League Championship. In 1908-09 he found opportunities limited and made only 5 more appearances for The Owls before joining Southern League Swindon Town in June 1909.
Bolland became an important player at The County Ground, helping Swindon to win the Southern League Championship in 1910-11 when he made 19 League appearances, although he didn’t play in either of Swindon’s FA Cup semi final appearances in 1910 or 1912, nor did he play in their 8-4 defeat to Manchester United in the 1911 FA Charity Shield. He missed only one match a season in the final two seasons before peacetime football was suspended after the outbreak of the First World War, but after the War he returned to the County Ground, and was again a regular in their 1919-20 Southern League campaign. When Swindon joined The Football League in 1920, Bolland made his final six appearances in the second half of their inaugural League campaign.
In May 1921, after 16 goals in 184 appearances for The Robins, he joined Bath City where he played until his retirement.