It was while at Chopwell that Waugh was spotted by Football League club Sheffield United who signed both Waugh and fellow defender Bill Sampy for a joint fee of £250 in April 1921. Waugh made a slow start to his career with the Blades and did not begin to feature regularly until November 1922, from which point he missed only one of the following 103 first team matches. Waugh was considered to lack pace and this caused him problems from 1925 when the offside rule was changed. A neck injury prevented Waugh from playing in the 1925 FA Cup Final and after a run of games at the start of the 1925–26 season he lost his place in the side to Seth King. Despite being selected for the FA tour of Canada in the summer of 1926, Waugh was unable to reclaim his place in United's starting eleven and was eventually transferred to Darlington in January 1927 after having made 143 appearances for the Blades and scored three goals.