Though Oldfield was at Maine Road for less than a year, he is fondly remembered for his two goals in the Manchester derby against local rivals United in September 1989 when City triumphed 5–1.

Oldfield was named as Oxford caretaker manager after the dismissal of Ian Atkins in March 2004 but his first game in charge was postponed due to bad weather[6] and Graham Rix was appointed before the next; Oldfield finally took charge of Oxford as caretaker manager for one game, a home defeat to Chester City, before the appointment of Brian Talbot in May 2005.

[8] Three days after Oldfield made his Tamworth debut, he was appointed as the new first team manager of Brackley Town on 4 December 2007, replacing Roger Ashby.

[12] On 12 June 2014, Oldfield joined Milton Keynes Dons as Head of Academy Coaching[13] He was appointed assistant manager to Jimmy Floyd Hasselbaink at Burton Albion in November 2014.

[14] Towards the end of the 2016–17 season Oldfield returned to Peterborough United on a trial basis after the departure of Lee Glover.

[15] He stepped in as caretaker-manager for one game in February 2018 after McCann's sacking, a 2–1 home victory over Walsall,[16] before Steve Evans was appointed.

[19] He left Weymouth by mutual consent on 14 September 2022 [1] In January 2025, Oldfield was named under-18 lead coach at Exeter City.