2019–20 Middlesbrough F.C. season
Date from Position Name To Fee Team
1 July 2019 DF Kieran Charlton Free agent Released Academy
1 July 2019 LM Stewart Downing Blackburn Rovers Free First team
1 July 2019 CB Nathan Guru Free agent Released Academy
1 July 2019 GK Dimitrios Konstantopoulos Hartlepool United Free First team
1 July 2019 GK Andy Lonergan Liverpool Free First team
1 July 2019 CF Gabby McGill Dunfermline Athletic Undisclosed Academy
1 July 2019 DM John Obi Mikel Trabzonspor Free First team
1 July 2019 CM Alex Pattison Wycombe Wanderers Free Academy
1 July 2019 CM Dan Ward Free agent Released Academy
17 July 2019 CB Kian Spence Scarborough Athletic Free Academy
19 July 2019 CB Aden Flint Cardiff City Undisclosed First team
24 July 2019 CF Martin Braithwaite Leganés Undisclosed First team
25 July 2019 CF Bilal Brahimi Stade de Reims Free Academy
26 July 2019 CF Luke Armstrong Salford City Undisclosed Academy
15 January 2020 GK Darren Randolph West Ham United £4,000,000 First team
31 January 2020 LB Patrick Reading Stevenage Undisclosed Academy
27 June 2020 ST Rudy Gestede Free agent Released First team
28 June 2020 CB Daniel Ayala Free agent Released First team
28 June 2020 ST Mitchell Curry Free agent Released First team
28 June 2020 CB Nathan Dale Free agent Released First team
Transfers -- Transfers out
The 2019-20 season is Middlesbrough's third consecutive season in the Championship in their 144th year in existence, the club will also compete in the FA Cup and the EFL Cup. This season marks Jonathan Woodgate's first spell in charge of a professional club, who replaced an outgoing Tony Pulis, who left at the end of his contract. George Friend continues as the official club captain in his first full season in the role, having previously replaced a departing Grant Leadbitter in the second half of the 2018-19 season, who left to return to Sunderland in January 2019.