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.
1. Thome raider
Popular Brazilian defender Emerson Thome celebrates scoring Wednesday's first goal in their 2-0 win over Stockport in the FA Cup Fourth Round win in January 1999. Photo: Craig Prentis
2. Two on Hughes
Mark Hughes, who was later to be tentatively linked with the manager's post at Hillsborough, squeezes through Jon Newsome and Steve Haslam as Southampton beat the Owls 2-0 at The Dell. Photo: Chris Lobina
3. Yorkshire derby days
Gilles De Bilde is wrestled to the ground by Leeds United's Jonathan Woodgate, now manager of Middlesbrough, in a Yorkshire derby that the Whites won 2-0 in October 1999. Photo: Michael Steele
4. In the presence of greatness
Petter Rudi and Danny Sonner pay close attention to Arsenal legend Dennis Bergkamp at Highbury. Photo: Ben Radford