Manchester United head into the final stages of the January transfer window tasting the bitter irony surrounding the remaining business they are looking to complete.

United are likely to only make one or two new additions to their squad before the transfer window shuts. Patrick Dorgu's arrival from Lecce appears to be on the verge of completion with the Reds keen to loan out Tyrell Malacia to make room for the Dane.

Mathys Tel could also join on loan but he is gathering interest from several Premier League clubs so United will not be holding their breath. While Tel and Dorgu will likely be good signings they are also dependent on players leaving the club.

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As mentioned, Malacia culd well be at the top of the list of players set to leave with Real Betis and, crucially, Benfica reported to be keen. Interest from the Portuguese giants would be particularly damning of United's transfer business in recent years.

Last January, United loaned Alvaro Fernandez (now Carreras) to Benfica before he completed a permanent switch to the club in the summer. Since then, the 21-year-old has not only become a regular domestically but also in the Champions League.

The Reds have a buyback option but currently cannot afford to activate it so they are stuck watching him move from strength to strength while United struggle down the left flank. Now, with Benfica linked with Malacia, it seems the Reds finally realise the talent they had.

Local Portuguese journalist Oscar Botelho has insisted the Dutchman would only be playing second fiddle to Carreras should he sign, leading to questions over why he was never given a chance at United. Erik ten Hag was not blessed with full-back options when he allowed the left-back to leave and his progression since then has shown that if anyone was to leave in that position, it should not have been him.

Now, United are having to invest again in that position to try and secure themselves for the future when they had the ready-made Malacia replacement in their ranks just 12 months earlier. If United are to progress, Ruben Amorim needs to cutback on these transfer errors - that have unfortunately been all too common for the club in recent years.