The Owls were relegated from the Championship last season following a points deduction and had the opportunity to bounce back at the first time of asking through the League One play-offs.
But unfortunately for Darren Moore's side, it wasn't meant to be, as his team fell to a 2-1 defeat on aggregate to promotion chasing Sunderland.
The South Yorkshire outfit got themselves back into the game in the second leg after trailing 1-0 from their trip to the Stadium of Light, scoring through a well worked move, rounded off by Lee Gregory.
However, the former Premier League club were left to rue their chances despite dominating the game, as Sunderland's Patrick Roberts put the final nail in their League One coffin in stoppage time.
Sheffield's passion for football runs deep through the city, including within the rivalry between Wednesday and their neighbours, Sheffield United.
And the friction between the two clubs is so strong that even former Blades keeper Aaron Ramsdale took to Twitter to indirectly comment on the Owls' loss on Monday night.
"Whoops," the Arsenal no.1 wrote, coupled with a laughing emoji.
The Steel City derby hasn't been played since March 2019, and whilst United sit in the league above Wednesday, nothing has separated the sides in their last three encounters - all of them ending in a 0-0 draw.
Despite this, though, former Crystal Palace chairman Simon Jordan believes it's actually the Owls that are the bigger club, despite the Blades being in the Championship play-offs.
"You find a club that's in League One, with that size and scale of a support base," the talkSPORT host said on Tuesday's White and Jordan show referencing the huge following the Hillsborough side enjoy.
"There's this debate of whether they're bigger than Sheffield United in terms of size - they are."
The Blades were in the Premier League as recently as last season, achieving an impressive 9th place finish in the campaign prior to that.
On the other hand, Sheffield Wednesday have been in the Championship and below since 2000. However, the Owls have experienced plenty of success, playing in the UEFA Cup in the 90s and beating Manchester United to win the League Cup in 1991.
And the former Crystal Palace chairman went on to the explain that this was part of the reason why Wednesday are the bigger club.
He continued: "They're not bigger than Sheffield United in terms of achievements in the last 25 years.
"In terms of the size of the stadium, in terms of the size of the support base, in terms of the achievements of the last 30 or 40 years, I think that's absolutely right."