On 8 August 2019, Maddox joined Tranmere Rovers on a season loan deal.[6][7] After two EFL Trophy appearances the loan was ended on 12 December 2019.[8]
On 12 August 2020, Maddox signed a four-year deal at Portuguese club Vitória de Guimarães, ending his seven year stay at Chelsea.[11] He returned to England in July 2021, signing on loan for Burton Albion.[12][13]
In September 2022 he signed for Walsall.[14][15] He was released by Walsall at the end of the 2022–23 season.[16]
^Veevers, Nicholas (26 April 2017). "Chelsea 5–1 Man City". The Football Association. Archived from the original on 10 October 2018. Retrieved 10 October 2018.
^Walker, Andy (15 July 2017). "Portugal 1–2 England U19s". The Football Association. Archived from the original on 24 March 2019. Retrieved 10 October 2018.