[3] In 1945, he began working at a Nottingham hosiery factory and was spotted playing football on his lunchtime break by Mansfield Town manager Roy Goodall in February 1947.
In January 1950, at age 23, he joined Stoke City after Bob McGrory offered Mansfield manager Freddie Steele £8,000 plus Verdi Godwin.
Oscroft hit ten goals in 39 games in 1952–53 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.
City suffered six games losing streak in which they failed to find the net late into the 1956–57 campaign, which ultimately cost them promotion; Oscroft still managed 12 goals in 42 appearances throughout the season.
A prolific goalscorer, averaging nearly one goal in every three games during his ten years at the Victoria Ground, he made 349 appearances.
[1] He hit seven goals in 29 appearances in 1959–60, including four in the final day of the campaign in a 6–1 hammering of Swindon Town at Vale Park.