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.
13. Old Trafford, same problems
Paul Scholes scores the first in a 4-0 drubbing at the hands of Manchester United at Old Trafford back in August 1999. Photo: Shaun Botterill
14. RIP Pavel Srnicek
Czech goalie Pavel Srnicek joined the club in 1999 and deputised for Kevin Pressman. Here he shouts the orders in a 2-1 defeat at Aston Villa He tragically died in December 2015. Photo: Ben Radford
15. Bye bye Beni
That same match saw Wednesday line up against former talisman Benito Carbone, who had left the club some months earlier. Photo: Ben Radford
16. Helpless
Wednesday manager Danny Wilson looks on during the hapless 4-3 defeat at Upton Park. Photo: Craig Prentis