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.
5. RIP Gary Speed
September 1999 saw Sheffield Wednesday fall to a humiliating 8-0 defeat to Newcastle United at St James Park. Here, Niclas Alexandersson battles the late Gary Speed for the ball. Photo: Clive Mason
6. A worrying early sign
Wednesday's 1-1 draw at Bradford City was a concerning early sign of what was to come back in August 1999. Here, Emerson Thome upends City's Dean Windass. Photo: Ben Radford
7. Horror show on and off the field
The Owls had only one win in the league by the time Watford arrived at Hillsborough in November, but they were able to pick up their sixth point of the season as Gilles De Bilde scored both goals in a 2-2 draw. Photo: Mark Thompson
8. Staring down
Keeper Kevin Pressman seems to sum up the feelings on an entire football club as he stares at the ground during Wednesday's 4-3 defeat at West Ham in November 1999. Photo: Mike Hewitt