Financial turmoil and relegation to League One twice have blighted the club as a succession of managers have tried and failed to bring back top flight football to Hillsborough.
But which Owls boss can claim to be the club’s most ‘successful’ this century? We take a look at the records of the 14 men who have been in the Wednesday hotseat since Peter Shreeves failed to save the club from relegation in the 1999/2000 season.
13. Jos Luhukay, February 2018 to December 2018
Luhukay lasted less than a year at the helm at Hillsborough and was sacked by Wednesday after a run of only one win and seven defeats in 10 games ,with the team sitting 18th in the Championship table.
The Dutchman had a win percentage of just 33.33 per cent, winning 16 out of 48 games. He also lost 13 and drew 19. Photo: Matthew Lewis
14. Steve Bruce, February 2019 to July 2019
Bruce incurred the wrath of Wednesdayites when he walked out on the club to become manager of his boyhood club Newcastle United just five months after taking on the top job at Hillsborough.
The former Manchester United skipper guided the Owls to seven wins from his 18 games in charge, with a 38.89 per cent win ratio. Photo: Nathan Stirk
15. Garry Monk, September 2019 to present
Monk is the latest man to be given a chance to change Wednesday's fortunes. But since guiding the Owls to third place in the Championship at Christmas, he has overseen a wretched run of form which has seen his side slip to 15th having won only won two of their 14 league games since Boxing Day.
He has a win percentage of 32.26 having won 10 out of 31 games to date. Photo: Alex Livesey