An architect by profession, Woodward began his career at Clacton Town. Following spells at Harwich &amp; Parkeston and Chelmsford, he joined Tottenham Hotspur in 1901, who that year would win the FA Cup. Due to work and cricket commitments, he wouldn't begin to appear regularly for the team until the 1902–03 season. In 9 seasons at White Hart Lane, he made 169 appearances and scored 73 goals. Tottenham was elected to the Second Division of the Football League for the 1908–09 season, and Woodward scored Spurs' first ever goal in the Football League in September 1908 against Wolverhampton Wanderers that finished 3–0. He helped the team win promotion to the First Division that season.