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...
17. Kim Olsen
Wednesday paid an – albeit small – transfer fee for the Dane in January 2004, but he returned to Denmark a year later as a free transfer after making just 10 appearances without scoring. Photo: Steve Ellis
18. Tyreece John-Jules
The young forward is doing fine things at Ipswich Town this season, and to be honest he makes this list through no real fault of his own. John-Jules came to Wednesday as a very exciting young signing, but played just 18 minutes due to injury and wasn't able to help play his part in a promotion push. Photo: Steve Ellis