The discussion highlighted a generational divide in what 'greatest' means: for some, it’s about pure goalscoring and longevity (Hirst); for others, flair and creativity (Waddle); and for others still, club loyalty and leadership (Sheridan, Bannan).
But whatever their era, every name shared by the fans sparked a passionate memory. As The Star continues to track the conversation, one thing is clear: for Wednesday supporters there may never be just one 'greatest' - but there are many heroes worth celebrating.
Inevitably there will be many great players that you feel should have made the top 25 - the names listed are the ones who were repeatedly nominated by our readers.
Let us know via the conversation on Facebook which ones you would have included and why.
1. Paolo Di Canio
Paolo Di Canio was a versatile forward - equally at home dropping deep or leading the line - and in 41 appearances for the Owls he netted 15 league goals, earning adoration from Wednesday fans for his technical brilliance and flair. | Getty Images
2. Chris Waddle
Chris Waddle arrived at Hillsborough in 1992 and, over the next four years, became a fans' favourite thanks to his dazzling dribbling, long-range strikes and creative spark. He made over 100 appearances for the Owls and was deservedly named FWA Footballer of the Year in 1993 after helping Wednesday reach both domestic cup finals. | Getty Images
3. John Sheridan
John Sheridan - the classy Irish midfielder - netted 25 goals in 199 appearances for Wednesday, but is most fondly remembered by fans for his thunderous winner in the 1991 League Cup final at Wembley, which sealed a 1-0 win over Manchester United. | Getty Images
4. Derek Dooley MBE
Derek Dooley MBE - a legend on both sides of Sheffield - was a fearsome striker for Wednesday, scoring 62 goals in just 61 league games. His career was tragically cut short when a serious leg fracture led to gangrene and eventual amputation. Despite that, he returned to football in other roles - managing Wednesday in the early 1970s and later becoming a long-serving executive at Sheffield United. | Sheffield Wednesday FC