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Under the stewardship of Roy Goodall, the "Stags" finished eighth in the Third Division North in 1947-1948, tenth in 1948-1949, and eighth again in 1949-1950.
Under the stewardship of Roy Goodall, the "Stags" finished eighth in the Third Division North in 1947-1948, tenth in 1948-1949, and eighth again in 1949-1950.
A left-winger, he scored over 150 goals in nearly 500 league games in a 14-year career in the Football League. He played for Mansfield Town for three years, before signing for Stoke City in January 1950. He made 349 appearances and scored 106 goals for the "Potters", before he was traded to Portuguese Vale in September 1959.
He left the "Valiants" in May 1961, and later turned out for non-league clubs Brantham Athletic and Sutton United.
Oscroft began his career with Mansfield Colliery, before moving on to Sheffield United and then Mansfield Town in 1947. He scored 39 goals in 112 league games during his spell at Field Mill.
In January 1950, at age 23, he joined Stoke City after Bob McGrory offered Mansfield manager Freddie Steele £8,000 plus Verdi Godwin. He scored three goals in 16 First Division games in 1949-1950.
He hit six goals in 39 appearances in 1950-1951, before hitting 10 goals in 44 games in 1951-1952.
McGrory was then replaced as manager by Frank Taylor. Oscroft hit ten goals in 39 games in 1952-1953 to become the club"s top scorer, as the "Potters" were relegated into the Second Division after finishing one point behind 20th place Manchester City. He bagged 13 goals in 36 appearances in 1953-1954, before hitting 21 goals in 38 games in 1954-1955 to become the club"s top-scorer for a second time.
Oscroft hit 18 goals in 43 games in 1955-1956, becoming the club"s joint-top-scorer, along with Frank Bowyer and Johnny King.
City suffered a six games losing streak in which they failed to find the Netto late into the 1956-1957 campaign, which ultimately cost them promotion. Oscroft still managed 12 goals in 42 appearances throughout the season.
He was limited to 22 games and seven goals in 1957-1958. A prolific goalscorer, averaging nearly one goal in every three games during his ten years at the Victoria Ground, he made 349 appearances and scored 106 goals, becoming the club"s sixth highest goalscorer of all time (as of 2012).
He hit seven goals in 29 appearances in 1959-1960, including four in the final day of the campaign in a 6–1 hammering of Swindon Town at Vale Park.
He scored five goals in 21 Third Division games in 1960-1961, and was handed a free transfer by the "Valiants" boss Norman Low in May 1961. Oscroft was known to often going "missing" during games, but could often could up moments on inspiration for his team He possessed a powerful left foot shot.
He then played a few games for Sutton United and finally retired from the game completely in 1988 and lived near Colchester.
He died in his sleep on 31 December 2008 after being cared for at home by his family. He had been suffering from Alzheimers for a number of years before he died.