Playing mainly on the wing for the Pars, in April 1959 he set a record for a winger, scoring six times in a 10-1 victory over Partick Thistle.
Three of Harry`s 106 goals were scored in European competitions, the most important of which was the goal 3 minutes from time, which knocked Everton out of the 1962/1963 Inter City Fairs Cup. Running on to a 50 yard defence splitting pass from Willie Cunnningham, Harry took the ball in his stride, and coolly ran in on goal to slot the ball past Gordon West in the Everton goal. Harry played in two of the Pars three Scottish Cup finals, in 1961 and in 1965, when despite Harry scoring the game’s first goal, the Pars narrowly lost 2-3 to Celtic. The following season, Harry made just one appearance for the Pars before he was transferred to Aberdeen for £10,000 in October 1965.
With the club`s fortunes in decline, Harry returned to East End Park to manage the Pars between 1975 and 1980. His finest moment in charge came in May 1979, when Dunfermline gained promotion to Division One, following a 1-1 draw against Falkirk in the last match of the season.