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The signings of Josh Windass and Callum Paterson shaped the frontline at Hillsborough for half a decade

Not many Sheffield Wednesday fans look back fondly on the last five years of Dejphon Chansiri's time at the club, as those resemble the worst of their financial troubles, which eventually ended in the club being placed into administration in October 2025.

However, there's no doubting that the period between 2020 and 2025 saw some Hillsborough cult heroes made, as the Owls, who suffered relegation, navigated life back in League One en route to a dramatic promotion and then incurred a mighty struggle to stay alive in the second tier upon their return.

Two of the leading scorers in that period, Josh Windass and Callum Paterson, were brought in permanently during the summer of 2020 by Gary Monk in his final few moments as Wednesday boss, before he was sacked later that year in November.

Monk may not have lasted long enough to see the two frontmen excel at Hillsborough, but Wednesdayites were treated to the line-leading duo for half a decade.

The likes of Liam Palmer, Barry Bannan and Dominic Iorfa are often regarded as the long-standing Wednesday heroes of the past 10 years, but both Windass and Paterson deserve plaudits for their contributions, too.

Josh Windass' successful stint at Sheffield Wednesday

Windass initially made his move to Wednesday on loan in January 2020 from Wigan Athletic, who were just six months out from being placed into administration during the height of the COVID-19 pandemic.

It made sense for the move to be made permanently ahead of the 2020/21 campaign, not only as Windass netted three in just 9 games during the second half of the 2019/20 season, but also because the Owls needed all the help they could get to overturn a points deduction of their own.

Indeed, Wednesday were docked an initial 12 points ahead of the new term, due to the previous breaking of spending rules. While this would eventually be cut to just six points, it meant that backs were against the wall immediately.

The Owls would end up being relegated due to this deduction, having finished three points adrift of safety. However, Windass did his best to help keep the club afloat, scoring a team-high nine goals and contributing six assists alongside that in his first season.

After his most productive year back in England since he departed for Rangers in 2016, everything was pointing towards Windass having a great year in League One. However, various long-term injuries restricted him to just nine league games all season, and just three starts.

Despite this, he still ended up with six goal contributions, and when Wednesday fell in the play-offs against Sunderland, various 'what if's' floated about as to how far that team could have gone if the then-28-year-old could have been fit for the majority of the campaign.

Those questions were answered the following season, when Windass missed just 12 league games, registering 11 goals and seven assists across the League One season.

The miraculous play-off run in 2023 is well-documented, and while the frontman didn't score in the famous semi-final turnaround against Peterborough United, his heroics were saved for the final, where his 123rd-minute winner against Barnsley sent the Wednesday half of Wembley into delirium and secured the Owls' return to the Championship.

Back in the second tier, Windass began to re-establish himself as a serviceable Championship attacker. While injuries once again restricted him during the first season back, his 13 goals in the 2024/25 campaign, his final one for the club, were the second-best scoring return of his entire career.

Callum Paterson was a reliable frontman at Sheffield Wednesday

Paterson began his time at Hillsborough in the limelight. Just a couple of years ago, he was playing in the Premier League, and the season prior, he was in the Championship play-offs with Cardiff City, so he was seen as more of a marquee signing.

And, while he may not have provided the goalscoring threat that Windass did, he was still a well-liked figure at Hillsborough.

Paterson's most productive campaign in front of goal came in his first. The former Cardiff frontman netted eight times in 43 games, but couldn't help the Owls overturn the points deduction needed to stay up.

The relegation to League One saw the versatile frontman battling with a plethora of attacking talent for regular starts, including new signing Lee Gregory. Paterson played several positions all across the pitch that year and scored six times.

Unfortunately, he barely got a look in during their subsequent play-off defeat, playing just 12 minutes across both legs in the defeat to Sunderland. The year after, though, he'd be one of the main characters in the miracle of Hillsborough.

Paterson nearly equalled his scoring tally from the previous League One campaign in 15 fewer games, netting five in 25 during the regular season. In the play-offs, he played the entirety of the dramatic play-off semi-final win over Peterborough, assisting Gregory for the second and then scoring the equaliser in extra time to send the game to penalties.

Ultimately, Windass would take the plaudits for his goal in the final, but Paterson's efforts in the semi-final turnaround helped set the stage for that play-off final win.

He may have fallen out of contention for the majority of Danny Rohl's time in charge at Hillsborough, and a knee injury in February 2024 didn't help with that, but a lengthy spell in the side towards the tail end of the 2024/25 campaign, starting 11 of the final 12 games, helped Paterson end his time at Hillsborough on a high.

Josh Windass and Callum Paterson left Sheffield Wednesday in less-than-ideal circumstances

Both Paterson and Windass departed the club in the summer of 2025 amid plenty of off-field controversies at Sheffield Wednesday towards the tail end of Dejphon Chansiri's time as chairman.

Paterson's contract was up at the end of the 2024/25 campaign, and after rejecting an initial offer to extend, the then 30-year-old didn't receive another proposal, and thus left as a free agent, signing with MK Dons in League Two.

As for Windass, who signed a new contract ahead of the 2024/25 season, he was one of the various Wednesday players who mutually departed the club following several late wage payments across that summer, which bled into the start of the 2025/26 campaign.

Despite a rocky end to their tenures, both Windass and Paterson remained popular figures, and their contributions to the side's play-off triumph in 2023 will never be forgotten at Hillsborough.

It may not have always been smooth sailing during their five years at Sheffield Wednesday, but there's no doubting that the club hit the jackpot with their initial arrivals in 2020.