Boro made four new signings during the window, as goalkeeper Tomas Mejias, Marcus Browne, Marc Bola and Anfernee Dijksteel all signed for the club. We take a closer look at some of the players who got away and how they’ve fared since. Scroll down and flick through our gallery to find out:
1. Jamal Lowe (Wigan)
After an impressive spell at Portsmouth in League One, the winger was linked with several Championship clubs in the summer. Wigan finally got a deal over the line and Lowe has featured in all 11 league games for the Latics this season. However, he is still yet to score for a struggling side.
Photo: Jordan Mansfield
2. Josh Koroma (Huddersfield)
The forward has played just 11 minutes of Championship football after making the step up from Leyton Orient to Huddersfield. At 20-years-old , he still has time to develop though.
Photo: George Wood
3. Sheraldo Becker (Union Berlin)
Boro were linked with the pacey wideman before the arrival of Jonathan Woodgate. But, instead of signing for the Teessiders, Becker, 24, joined German side Union Berlin. The Dutchman has played regularly in the Bundesliga yet his new side have won just one of seven league games.
Photo: Robertus Pudyanto
4. Tom Bayliss (Preston)
Another player who was linked with several clubs. The midfielder, 20, eventually joined Preston but has only appeared in their three Carabao Cup fixtures.
Photo: Nathan Stirk