Assessing Middlesbrough's last five transfer windows - and the lessons Jonathan Woodgate must learn

Middlesbrough manager Jonathan Woodgate has so far made two loan signings this January, with Patrick Roberts and Lukas Nmecha joining from Manchester City until the end of the season.

Wednesday, 15th January 2020, 4:45 pm
Updated Wednesday, 15th January 2020, 4:50 pm
Jordan Rhodes during his time at Middlesbrough

But how have Boro fared in their last five transfer windows? Below we look at who they’ve signed and how much they’ve spent, and rate how successful each window has been for them.

Summer 2019


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Tomas Mejias (Omonia Nicosia) Free

Marcus Browne (West Ham United) £200k

Marc Bola (Blackpool) Undisclosed

Anfernee Dijksteel (Charlton Athletic) £2m


Stewart Downing (Blackburn Rovers) Free

Dimitrios Konstantopoulos (Released)

Andy Lonergan (Liverpool) Free

John Obi Mikel (Trabzonspor) Free

Aden Flint (Cardiff City) £4m

Martin Braithwaite (Leganes) £9m


While getting £9m for Martin Braithwaite was a success given he didn’t feature on a regular basis for Boro last season, they lost a key defender in Aden Flint and didn’t really replace him.

Both Marcus Browne and Marc Bola have been loaned out this month due to a lack of first team football, and Tomas Mejias has only made one appearance all season so whether they have been effective signings is questionable.

Anfernee Dijksteel has made 13 appearances during his time at the club so far, but there hasn’t been any outstanding signings from the summer that have shined so far this season.

January 2019


George Saville (Millwall) £7m

John Obi Mikel (Tianjin TEDA) Free

Rajiv van La Parra (Huddersfield) Loan


Connor Ripley (Preston North End) Undisclosed

Grant Leadbitter (Sunderland) Free


The signing of George Saville on a permanent deal after he joined on loan the previous summer has proved to be a relative success with the midfielder being a regular in the side. He has scored five goals in 57 appearances so far.

The arrival of experienced midfielder John Obi Mikel proved to be a major shock but he didn’t really make a real impact scoring just once in 19 appearances.

A fairly uneventful window for Boro but they got good value for money.

Summer 2018


Aden Flint (Bristol City) £7.2m

Paddy McNair (Sunderland) £5m

Andy Lonergan (Leeds United) Free

Jordan Hugill (West Ham United) Loan

Mo Besic (Everton) Loan

Sam McQueen (Southampton) Loan

Danny Batth (Wolves) Loan

George Saville (Millwall) Loan


Antonio Barragan (Real Betis) £900k

Martin Cranie (Released)

Tomas Mejias (Omonia Nicosia) Free

Fabio (Nantes) £1.8m

Patrick Bamford (Leeds United) £7m

Ben Gibson (Burnley) £15m

Adama Traore (Wolves) £18m

Julien De Sart (KV Kortijk) Free


Boro lost three key players in the summer of 2018 in Bamford, Gibson and Traore and while Gibson and Bamford were replaced in the signings of Flint and Hugill, arguably their biggest loss Traore wasn’t replaced.

And Hugill’s impact at Boro was limited with just seven goals in 41 appearances, but Flint proved to be a regular partner of Daniel Ayala at centre-back.

Paddy McNair didn’t really justify his price tag last season as he was slightly out of favour under Tony Pulis making just 16 league appearances, but he has been more of a regular under Jonathan Woodgate more recently.

January 2018


Martin Cranie (Huddersfield) Undisclosed

Jack Harrison (Manchester City) Loan

Mo Besic (Everton) Loan


Adam Forshaw (Leeds United) £4.5m

Cyrus Christie (Fulham) £3m

Adlene Guedioura (Nottingham Forest) Free


Martin Cranie and Jack Harrison were poor signings for Boro making just 13 appearances between them, and Cranie was released at the end of the season. The fact that Boro paid a fee for Cranie is a failure in itself given he was released.

However, Muhamed Besic proved to be impressive at Boro leading to him being brought in again on loan at the start of the following season and was the ideal replacement for Adam Forshaw at the time.

Cyrus Christie didn’t last long at Boro before being poached by Fulham and it was right for Guedioura to leave as he only made six appearances over one-and-a-half seasons at the club.

Summer 2017


Lewis Wing (Shildon) Free

Cyrus Christie (Derby County) £2.5m

Jonny Howson (Norwich City) £5m

Martin Braithwaite (Toulouse) £10m

Britt Assombalonga (Nottingham Forest) £15m

Darren Randolph (West Ham United) £5m

Ashley Fletcher (West Ham United) £6.5m

Ryan Shotton (Birmingham City) £2.9m

Marvin Johnson (Oxford United) £2.4m

Connor Roberts (Swansea City) Loan

Lewis Baker (Chelsea) Loan


Jordan Rhodes (Sheffield Wednesday) £10.5m

Viktor Fischer (Mainz 05) £2.7m

Brad Guzan (Atlanta United) Free

Bernardo Espinosa (Girona) £4m

James Husband (Norwich City) £990k

Cristhian Stuani (Girona) £2.25m

Gaston Ramirez (Sampdoria) £8.1m

Alex Baptiste (Released)

Marten de Roon (Atalanta) £12.2m


Many of the signings that Boro made during the summer of 2017 remain in the squad now and have made a major impact - in particular Britt Assombalonga has since made 114 appearances for Boro during his time at the club and scored 37 goals. Whether that means he’s justified his £15m price tag however is debatable.

Lewis Wing has proved to be a good acquisition over time, especially as they didn’t have to pay a fee to Northern League club Shildon and he is a regular in the squad now having played in 24 of Boro’s 27 Championship games so far this season.

Boro also got decent money for the likes of Jordan Rhodes, Gaston Ramirez and Marten de Roon, making up for the fact they spent nearly £50m in this window.