The Owls, like most clubs, have been very hit and miss in the winter transfer window, signing some quality players and also making some mistakes in the market since transfer windows were introduced officially by FIFA ahead of the 2002/03 season.
With the winter window now just a few weeks away we took a look back at some of the best – and worst – acquisitions at Hillsborough since then, and there are some corkers...
9. Marcus Tudgay
One of only two players this millennium to score 50+ goals for the Owls, and became a double centurion at the club with more than 200 appearances to his name. His goal against Sheffield United is fondly remembered. Photo: Steve Parkin
10. Achraf Lazaar
His ability was never in doubt, but with only four appearances during his loan spell at Hillsborough, Wednesdayites saw one exciting showing and then lost him to a series of injuries. Photo: Steve Ellis
11. Owls Jordan Rhodes. Pic Steve Ellis
The club’s record signing racked up over 100 appearances for Wednesday over the years, but his goal return of just 20 goals is far from what the club expected given the money they forked out. Not great bang for their buck. Photo: Jordan Rhodes
12. Callum McManaman
Was seen as quite an exciting signing under Carlos Carvalhal, but only made a handful of starts and got just two assists and no goals during his spell at Hillsborough. Photo: Steve Ellis