Sheffield Wednesday Woodhead had signed full professional terms with Sheffield Wednesday in April 1945 whilst still on active war service and he made his debut for the club on 24 May 1947 shortly after leaving the RAF. He played the last three games of that 1946–47 season as Wednesday managed to avoid relegation from
Division Two. The following two seasons saw Woodhead miss only eight league matches as he made the left wing position his own. However, on the first day of the 1949–50 season (20 August) he broke his right leg in a 3–1 victory over
Leicester City and did not return to the first team until the
Christmas Eve home match against
Bradford City where he scored a late equaliser. The fine form of Walter Rickett kept Woodhead out of the side for much of the remainder of the season although he did return for the vital last few matches of the campaign as Wednesday gained promotion to the
First Division. Woodhead returned as a regular to the team in the following season in Division One, scoring 14 goals and ending as joint top scorer with
Hugh McJarrow and
Redfern Froggatt. Woodhead played the last nine games of the campaign as a stand-in centre forward, scoring nine goals as Wednesday struggled in attack and were eventually relegated. The start of following season saw Woodhead again playing at centre forward, scoring seven goals in the opening nine games before picking up a bad injury. This allowed
Derek Dooley to force his way into the side, scoring an amazing 46 goals in 30 appearances as Wednesday lifted the Second Division championship. Woodhead remained first choice left winger for the following two seasons in Division One, doing especially well in 1953-54 when he top scored with 21 goals including three in the FA Cup as Wednesday reached the semi-final where they lost to
Preston North End at
Maine Road. The 1954-55 campaign saw Woodhead lose his regular spot in the team as Wednesday had a disastrous season, being relegated by nine points. He was in and out of the team as
Alan Finney and
Jackie Marriott played in the wing positions and limited Woodhead to just ten appearances in his final season at
Hillsborough. Following relegation Wednesday manager
Eric Taylor decided to rebuild the team and brought in 20-year-old
Albert Broadbent from
Notts County as a replacement for the 30-year-old Woodhead.
Latter career Woodhead was signed by Chesterfield manager
Teddy Davison for a fee of £2,000 on 9 September 1955 and made a thrilling debut scoring three goals in a 7–2 home win over
Rochdale. He was selected to play for the
Third Division North team against the South in 1955/56. However his stay at
Saltergate lasted only four months, making 16 appearances in total before joining
Derby County in January 1956 for a fee of £1,500. Woodhead had three good seasons with Derby, helping them to promotion from
Division Three North in 1956-57 when he scored 14 goals. In February 1959 he was sold to
Southport for £750 but the move only lasted four games after it was found that Woodhead had an ongoing knee injury and he was instructed to return to Derby by
The Football League after a month. Woodhead retired from full-time League football in May 1959. ==After playing==