Boro are chasing promotion under manager Aitor Karanka, who was famously Jose Mourinho's assistant at Real Madrid before leaving the club for a shot at management himself at the Riverside Stadium. Whilst a return to the Premier League is the ambition, results so far have been indifferent at best, with two wins and three defeats from their first five Championship games.
The club have spent heavily this summer, bringing in the likes of Tomas Mejias, Damia Abella, Kike, Emilio Nsue, Yanic Wildschut and Jelle Vossen, but the club have also taken advantage of Karanka's relationship with Mourinho by loaning a number of Chelsea players.
Goalkeeper Jamal Blackman, defender Kenneth Omeruo and striker Patrick Bamford have all arrived from Stamford Bridge on loan, whilst Nathaniel Chalobah joined the club on loan last season, with the North East club becoming something of a feeder club for Chelsea.
Now, the three Blues players current on Teesside could be joined by another, as Boro line up a move to sign midfielder Lewis Baker. The 19-year-old has bagged nine goals in 14 games for the England Under-19 side, and is highly rated by Mourinho - which is reportedly holding up a loan deal for the youngster.
Karanka wanted Baker to become the latest player to make the move to the North East, but thin ranks in midfield at Stamford Bridge means Mourinho wants to keep hold of Baker - for now. The Blues have Cesc Fabregas, Nemanja Matic, Ramires and John Obi Mikel, but after seeing Chalobah join Burnley on loan, Baker may be needed as cover.
It's disappointing for Middlesbrough and for the player himself. Omeruo and Bamford certainly benefited from loan moves to Championship clubs last season, and Baker would too - and under the guidance of Mourinho's closest football friend, he could have flourished.
Yet for now, he must be content with a place on the sidelines at Chelsea.