He made his debut as an amateur, on 19 January 1947, against West Bromwich Albion. His footballing skills flourished under new manager Arthur Rowe who was developing his push and run side which at the time was challenging for promotion to the First Division. He formed a good understanding with Les Medley on the left, and was a key player in the side that won the Second Division title in 1949–50. "Spurs" continued to win games, and were crowned champions of England in 1950–51, finishing four points ahead of second place Manchester United. In 1951–52 the situation reversed, as "Spurs" finished runners-up, four points behind United. On 2 April 1952, in a match against Huddersfield Town at White Hart Lane, Baily caused controversy after he took a corner kick by hitting the ball against the referee, before crossing it into the box for Len Duquemin to score the winning goal. After a tenth-place finish in 1952–53, Tottenham continued to slide down the table, and battled just above the relegation zone in 1954–55 and 1955–56. During his time at "Spurs", Baily made 325 appearances in the league and FA Cup, scoring 69 goals.