After leaving school, Hendry, a talented forward, played for Dunblane Thistle and then Dundee Wanderers, usually at outside right, but he was soon to play football in England. There was no professional football at the time in Scotland, so those players with talents to sell crossed the border. In 1888, Hendry found himself playing for West Bromwich Albion in the first Football League season. Hendry made his League debut on 8 September 1888, in a 2–0 win against Stoke at the Victoria Ground. Hendry scored his debut League goal on 29 September 1888 at Stoney Lane, against Burnley. He played 16 of the "Throstles" 22 Football League matches and scored three goals in 1888–89. Hendry, now playing as a centre forward was restless in his time with the Baggies, and in April 1889 he joined Stoke. While at Stoke Hendry was mainly used as a left-back and played 16 times scoring once. In January 1890 he joined PrestonNorth End, who had just become Football League champions for a second time.
Sheffield United
In January 1891, Charles Stokes, the Chairman of Sheffield United's football committee went to Preston and returned with the signatures of three Preston players in the hope of improving United's professionalism. The players he signed were Jack Drummond, Sammy Dobson and Billy Hendry. Hendry made his debut for Sheffield United against Derby Junction on 28 February 1891 in a Midland Football League match. It was Drummond who was to score the goal that took the Baldes into the First Division in 1893, but it was Hendry's signing that was the most significant. By now, Hendry had become a centre half. He was made team captain at Sheffield United and remained so until his career with the club ended in 1895. He was a small stocky player, described as neat, cool and calculating with 'exceptional skill'. His value to Sheffield United lay not just in the shrewdness and effectiveness of his play, but in the direction and leadership he gave to the club in the early years of Sheffield United in general. The United committee "set great value upon his options as to the arrangement and formation of the team, and placed confidence in his judgement... and ability as a player, a captain, and an adviser" It was also said that Hendry's advice and guidance helped the natural talents of Ernest Needham, who was to become an England international. Hendry sustained an injury during a New Year's Day friendly fixture at Leith Athletic in 1895 and it was thought that it would end his career. He played only four more games for United before being released the following summer.
