Boro's worst 'repent at leisure' deadline day deals?

From collection above it appears our deadline day additions have generally not turned out well.

Possibly mentioned elsewhere but have there been ANY good ones?
 
MickaelDebevePhenomenal said:
Whoa!!!! Debeve was signed as an unattached player in February 2002. (And what a signing)

The Jan window was introduced in the 2002/2003 season, so Jan 2003
Click to expand...
The highs and lows of Boro.

Highs; just inserted Mark E Smith and Antonio Conte into an AI image generator and it spat out Michael Debeve.

Low; Having a look on TransferMarkt for our worst January signing, clicked filter by year - 09/10. I feel sad.
 
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