A prolific marksman in Stoke whilst an iron foundry worker, after a spell with Sandford Hill Phillips signed with Lincoln City with whom he scored on his league debut, the second goal in a 3–0 home win against Middlesbrough on the opening day of the 1899/1900 season.
He played for Stockton FC between 1900-03 where he was part of the FA Amateur Cup winning team of 1902/03.
He was signed by Grimsby Town in 1903, scoring 9 goals in 21 appearances. He finished the 1904/05 season as joint top scorer with seven goals despite missing several games with a knee injury. As reported in the March 27 edition of The Athletic News during a game against Glossop, "Phillips scored the best goal of the day after a fine run half the length of the field" whilst deputising at Outside Left for his teammate, William Ross.
His form during the 1904/05 season drew an unsuccessful £150 bid from Middlesbrough, though at the season's end he was allowed to join New Brompton (later to become Gillingham FC) as a free agent.
He was a versatile attacker, making appearances across the front line over the course of his career, with the majority being at centre forward.
In "Mariner Men: Grimsby Town Who's Who 1892-2007" by Rob Briggs and Dave Wherry, Harry is likened in style to Joe Rogers, described as "a bustler, quick on the ball, one of the cleverest with his head".