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.
17. Poyet v Briscoe
At the turn of the year Wednesday lost 3-0 to Chelsea in a match that saw Chelsea field an all-foreign side for only the second time in Premiership history. Dennis Wise, Tore Andre Flo and Jody Morris scored for the Londoners. Photo: Phil Cole
18. Getting handsy
Wednesday legend Des Walker gets to grips with the slippery Juninho during the Owls' 1-0 win over Middlesbrough on Boxing Day 1999. Photo: Tony O''Brien
19. Happy days
Petter Rudi celebrates his goal in the 4-1 win over Norwich City in the third round of the FA Cup way back in January 1999. Photo: Laurence Griffiths
20. Mackem pay
Owls boss Danny Wilson stands out with his staff during their 1-0 defeat at Sunderland in September 1999. Photo: Shaun Botterill