Bristol born inside forward Freddie Wilcox began his football career with Glendale in 1900 before joining Southern League Bristol Rovers in 1901, where he scored 18 goals in 48 appearances before joining Second Division Small Heath in March 1903. He made his Football League debut scoring twice in a 5-1 win over Blackpool at the end of the month. In his fourth game he scored 4 times as Small Heath beat Doncaster Rovers 12-0 in April 1903 equalling their club record victory, and at the end of the season they won promotion to the top flight finishing as Second Division runners up.
He then had three seasons playing with Small Heath in the top flight, scoring a hat-trick against Wolverhampton Wanderers in February 1905 and another treble against Nottingham Forest the same December, before Middlesbrough signed him in March 1906 after 32 goals in 84 appearances. He scored 12 goals for ‘Boro in his first full season at the club, with only Steve Bloomer ahead of him in the goalscoring charts, and was a regular for three seasons until losing his place in March 1909, after which he played only once more, making his final appearance of 110 for Middlesbrough against Chelsea in October 1909, having scored 22 goals for the club. He joined Southern League Plymouth Argyle in 1910 but didn’t make their first eleven, retiring soon thereafter.