Leo Castledine is receiving limited game time at Middlesbrough, having started just four games in nine months since his arrival in January 2026 for a fee of just under £1 million, and could depart in the upcoming transfer window. A January exit, either on loan or permanently, could be beneficial for the 21-year-old English attacking midfielder. His former club Huddersfield Town would likely be open to his return after a successful six-month loan spell where he scored 12 goals. It is suggested that Middlesbrough could potentially use Castledine as part of a deal to sign Huddersfield's Derensili Sanches Fernandes. Fernandes has reportedly attracted interest from other Championship clubs and teams in Europe. The midfielder, who has five caps and two goals for England U19, is under contract until 2030 and has a current Transfermarkt market value of €2.00m.