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.
As we head towards the 11pm deadline we took a look back at some of the best – and worst – acquisitions at Hillsborough since then, and there are some corkers...
5. Reda Johnson
Follow the Reda. A massive fan favourite at Wednesday, and a player that scored 19 goals in 88 games during his time at the club – a remarkable record for a defender. Still widely loved. Photo: Anna Gowthorpe
6. Lewis Buxton
Buxton signed permanently on in January 2009, and went on to make over 200 appearances for the club and won personal accolades for his performances. Played in loads of positions and helped the Owls to promotion. Photo: Steve Ellis
7. Jermaine Johnson
When Brian Laws signed ‘JJ’ in 2007, he automatically missed three games because of a red card in his last game for Bradford City. But he made up for lost time over the years, playing more than 250 games and contributing to 54 goals and assists for the club – another promotion favourite. Photo: Steve Ellis
8. 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