Many Sheffield Wednesday fans do not remember Dejphon Chansiri’s last five years at the club fondly, as they were the worst of the club’s financial woes, which eventually led to the club being placed into administration in October 2025.

However, there is no doubt that the era between 2020 and 2025 produced some Hillsborough cult heroes, as the Owls, who had been relegated, negotiated life again in League One en route to a spectacular promotion and then faced a huge struggle to stay alive in the second tier upon their return.

Gary Monk brought in two of the leading scorers from that period, Josh Windass and Callum Paterson, on a permanent basis in the summer of 2020, in his final few moments as Wednesday manager, before being fired later that year in November.

Monk may not have been around long enough to watch the two frontmen shine at Hillsborough, but Wednesday fans were treated to the line-leading tandem for half a decade.

Liam Palmer, Barry Bannan, and Dominic Iorfa are commonly seen as the long-standing Wednesday heroes of the past decade, but both Windass and Paterson deserve recognition for their achievements as well.

Josh Windass’ excellent spell at Sheffield Wednesday

Windass joined Wednesday on loan from Wigan Athletic in January 2020, barely six months after the club went into administration amid the COVID-19 pandemic.

It made sense to make the move permanent ahead of the 2020/21 season, not only because Windass scored three goals in just nine games during the second half of the 2019/20 season, but also because the Owls needed all the aid they could get to overturn their own points deduction.

Indeed, Wednesday was docked an initial 12 points ahead of the new term due to a previous violation of spending restrictions. While this would later be reduced to six points, it meant that the backs were against the wall right away.

As a result of this deduction, the Owls were demoted, finishing three points below safety. In his first season, Windass did his best to keep the club afloat, scoring a team-high nine goals and adding six assists.

Following his most productive year back in England since leaving for Rangers in 2016, everything pointed to Windass having a successful season in League One. However, a series of long-term ailments limited him to just nine league appearances this season, with only three starts.

Despite this, he contributed six goals, and when Wednesday lost in the play-offs to Sunderland, many ‘what if’s’ were tossed about as to how far that squad may have gone if the then-28-year-old had been fit for the rest of the campaign.

Windass answered those questions the next season, missing only 12 league games and scoring 11 goals and seven assists in League One.

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

Windass reestablished himself as a respectable Championship attacker in the second tier. While injuries limited him during his first season back, his 13 goals in the 2024/25 season, his final with the club, were the second-best scoring return of his career.

Callum Paterson was a solid frontman for Sheffield Wednesday.

Paterson began his stint at Hillsborough under the spotlight. He was playing in the Premier League a few years ago, and the season before that, he was in the Championship play-offs with Cardiff City, so he was seen as a marquee acquisition.

And, while he did not pose the same goal-scoring danger as Windass, he was a popular figure at Hillsborough.

Paterson’s most productive season in front of goal was in his first. The former Cardiff forward scored eight goals in 43 games but was unable to assist the Owls overcome the points reduction required to remain up.

Following his demotion to League One, the dynamic frontman competed with a multitude of offensive skill for regular starts, including new arrival Lee Gregory. Paterson scored six goals while playing in a variety of positions on the field that season.

Unfortunately, he received little playing time in their subsequent play-off defeat, appearing for only 12 minutes across both legs against Sunderland. However, the following year, he would play a key role in the Hillsborough Miracle.

Paterson nearly equalled his League One scoring total from the previous season in 15 less appearances, scoring five goals in 25 regular-season games. In the play-offs, he played the entire dramatic play-off semi-final victory over Peterborough, assisting Gregory for the second goal and then scored the equalizer in extra time to force penalties.

Windass would eventually receive the credit for his goal in the final, but Paterson’s efforts in the semi-final comeback helped pave the way for that play-off final victory.

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 matters, but a lengthy spell in the side near the end of the 2024/25 season, starting 11 of the final 12 games, helped Paterson finish his time there on a high note.

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

Both Paterson and Windass left the club in the summer of 2025, after numerous off-field scandals at Sheffield Wednesday at the end of Dejphon Chansiri’s tenure as chairman.

Paterson’s contract expired at the end of the 2024/25 season, and after declining an initial offer to extend, the then-30-year-old did not get any proposal, leaving as a free agent and joining with MK Dons in League Two.

Windass, who signed a new contract ahead of the 2024/25 season, was one of numerous Wednesday players who mutually left the club after multiple late wage payments during the summer, which lasted into the start of the 2025/26 season.

Despite a tumultuous end to their careers, Windass and Paterson remained popular figures, and their efforts to the club’s play-off victory in 2023 will be remembered at Hillsborough.

It may not have been easy sailing during their five years at Sheffield Wednesday, but there’s no denying that the club won the jackpot with their initial arrivals in 2020.