From Gilles De Bilde to Pavel Srnicek, there were a number of cult hero names to take part, pitted against some big names from clubs around the country.
Let’s take a look at 20 images that capture what was a challenging calendar year for the Hillsborough club.
9. Di Cani-who?
The 4-3 defeat pitted the Owls against former forward Paulo Di Canio, who scored a 62nd minute penalty as the Hammers came from 3-1 down to win the clash. Photo: Craig Prentis
10. Young blood
A young Wednesday fan watches on as the Owls collect their second league win of the season, a 1-0 win over Middlesbrough at home on Boxing Day 1999. Can anyone identify this youngster? Photo: Tony O''Brien
11. Bowing out
Jon Newsome tackles a young Keiron Dyer in that infamous 8-0 hammering in the north east. It would prove to be the lifelong Wednesdayites' final game. Photo: Clive Mason
12. Owen-ing it
That man Emerson Thome teams up with Des Walker in an attempt to crowd out Michael Owen of Liverpool at Anfield. The Reds won out 4-1. Photo: Michael Steele