Former defender Whelan was part of the Blackburn side that faced Wolves in the 1960 final at Wembley, but his involvement ended just before half-time - with his team 1-0 down through a Mick McGrath own-goal - when he broke his leg in a challenge with Wanderers winger Norman Deeley and was taken to hospital.
Rovers were left to play out the rest of the game with 10 men, and two goals from Deeley saw Wolves secure a 3-0 victory - something Whelan only found out from a doctor after emerging from the operating theatre later that afternoon, and which immediately reduced him to tears.
The 76-year-old - who still bears stud marks from the incident and says he has never received an apology from anyone at Wolves, but is sure Deeley did not mean to harm him - has been recalling memories of that day ahead of Wigan's FA Cup quarter-final against Everton at Goodison Park.
A trip to Wembley for what would be the Latics' first-ever appearance in the semi-finals of the competition awaits if they can get past the Toffees and Whelan, harbouring a sense of "unfinished business" from his past experiences, is dreaming of what his club can achieve this year.
Reflecting on the 1960 final, Whelan said: "I really fancied we would bring that cup away from Wembley and I didn't finish the match.
"I got my cup final medal - a loser's one. So I do feel a great sense of unfinished business.
"To be in a cup final is something really, really special. It is a dream, and I have still got the dream to get the business finished, pick up the FA Cup and bring it back to Wigan.
"If - and it is a big if - I could get the chance to lead Wigan to Wembley, for me, it would be something absolutely unbelievable."
Whelan, who has enjoyed success as a businessman since retiring from playing football, purchased Wigan in 1995 and has overseen the club's remarkable rise from the fourth tier to the top-flight, where they are now in their eighth successive season.
The Latics have been consistently involved in relegation battles over the past few years and they are engaged in another this term, currently lying 17th in the Barclays Premier League, separated from the drop zone by goal difference alone with 10 games to go.
Wigan manager Roberto Martinez has made it clear that while he is eager to see the team continue to progress in the cup, survival in the league has to be the priority.
And Whelan, although an FA Cup romantic, takes a similar view.
"I would never, ever want to sacrifice a place in the Premier League," Whelan said.
"Whatever we say, the Premier League is the biggest league in the whole world."
Spaniard Martinez, a former midfielder who played for Wigan between 1995 and 2001 and was brought back to the club by Whelan when he appointed him as manager in 2009, has spoken of his ambitions of making the Latics a top-10 Premier League outfit.
It is something Whelan believes could have been achieved this season if the squad had not been hit by so many injuries, and looking to the future, the chairman has stressed that even if Wigan do go down this year, Martinez will retain his backing.
Whelan said: "I think with the team we have, if they are all fit it is good enough to get into the top half of the Premier League.
"It is an ambition Roberto has and we really thought we could do it this year.
"But Lady Luck hasn't smiled on us in terms of injuries and we have had to bear it.
"If the worst did come to the worst this season and we got relegated, the fight would be on to get back immediately, and Roberto is the man to fight for us, there is no question about that."