Middlesbrough had a strong summer transfer window, bringing in Grant Hall, Chuba Akpom and Sam Morsy on permanent deals whilst Patrick Roberts signed on a season-long loan.
Duncan Watmore also signed for Middlesbrough on a short-term deal in November, but Boro will be hoping to get a few deals over the line in January if they are to make a push for promotion.
Here are five deals Middlesbrough failed to secure that they could revisit in the winter window.
1. Yannick Bolasie – Everton
After being frozen out at Goodison Park, Bolasie’s career looks to be in limbo. The deal for the DR Congo international looked to be materialising on transfer deadline day but nothing came to fruition. He would provide pace and trickery out wide, something which Boro seriously lack.
2. Phil Jones – Manchester United
Although wages could be a stumbling block in this one, Middlesbrough are short on numbers in central-defence and would benefit from signing a new player for their back line. Jones would provide a wealth of experience for Neil Warnock’s side.
3. Kamil Grosicki – West Bromwich Albion
Also linked to Nottingham Forest in the summer, Grosicki is a wanted man. He is not in Slavan Bilic’s plans at West Brom and he is expected to leave in January. Similarly to Bolasie, he would inject some well-needed pace and power in wide areas.
4. Baba Rahman – Chelsea
Another player who has been told he can leave the club is Baba Rahman at Chelsea. The left-back would slot straight into the first-team at Middlesbrough if he was to sign.
5. Lee Gregory – Stoke City
Boro’s lack of firepower up front looks to be a real issue. The long-term injury to Ashley Fletcher means Akpom and Britt Assombalonga are Warnock’s only options. Gregory would add more goals to this Middlesbrough side.
