Harry Healless was born in Blackburn on 10th February 1893. He played local football for Blackburn Athletic, Victoria Cross and Blackburn Trinity.
The club had won two first division championships in 1911-12 and 1913-14, but struggled in the post-war years and finished 20th (1919-20), 11th (1920-21), 15th (1921-22), 14th (1922-23) and 8th (1923-24).
Blackburn Rovers continued to struggle and finished 16th (1924-25), 12th (1925-26) and 18th (1926-27) in the Football League. His form remained good and on 31st March 1928 he was selected to play for England against Scotland. However, England was thrashed 5-1 and it was the last time Healless played for his country.
According to Mike Jackman (The Essential History of Blackburn Rovers): "Not the most skilful of performers, there was a tenacity about Healless that enabled him to be used in a variety of positions. His strong running, tough tackling and relentless work ethic endeared him to the powers that be. He eventually won a place in the half-back line and proved proficient in all three positions."
In 1926 Bob Crompton was appointed as manager of Blackburn Rovers. He began to build a team around star players, Henry Healless, Jack Roscamp and Syd Puddefoot. This brought a change in the fortunes of the club and they did very well in the FA Cup in the 1927-28 season. Blackburn beat Newcastle United (4-1), Exeter City (3-1), Port Vale (2-1), Manchester United (2-0), Arsenal (1-0) to reach the final at Wembley. Puddefoot and Roscamp both scored four goals in the earlier rounds.
Huddersfield Town were hot favourites to win the final. However, in the first minute Roscamp received a pass from Syd Puddefoot. He chipped the ball over the head of Ned Barkas. Billy Mercer, the Huddersfield goalkeeper, attempted to catch the ball. Roscamp collided with Mercer and the ball slipped out of his grasp and trickled into the empty net. Tom McLean added a second after 22 minutes. Alex Jackson got one back for Huddersfield but Roscamp scored his second and Blackburn's third in the 85 minute to give the underdogs a well-deserved victory.
Blackburn also did better in the First Division of the Football League: 1928-29 (7th), 1929-30 (6th) and 1930-31 (10th). Bob Crompton retired as manager in 1931. Healless joined the coaching staff the following year. During a period of thirteen years he had played in 360 league games for the club.
In 1935 Healless moved to Holland to coach the Alemio club. He also rejoined the B coaching staff in 1951 but left the job two years later.
Harry Healless died in 1972.