Steve Bruce???s side entertain Manchester United at the KC Stadium while relegation rivals Newcastle face West Ham at home as part of Survival Sunday live on Sky Sports.
Duffen, who was Hull chairman from 2007-10, was in the directors box in 2009 as they managed to avoid relegation in a similar situation, with Alan Shearer???s Newcastle side going down.
As with Sunday, Hull faced United that day and host the same side on Sunday knowing nothing less than a win and other results going for them will see them demoted to the Championship.
And if Sunderland can claim a point from either of their last two fixtures against Arsenal on Wednesday or away to Chelsea on the last day of the season, Duffen hopes history can repeat itself in a shootout between Hull and Newcastle.
He told Sky Sports News HQ: ???It was a slightly different position because we were above Newcastle going into that last game, so provided we at least matched their score we were going to be fine.
“We lost to Man United on the day and then had to wait for the result of the Newcastle game. I think Damien Duff scored an own goal which kept us up and sent them down.
???But there is quite an auspicious omen for Hull City, which is that when we won the play-off final in 2008, seven years ago, it was the 24th of May and it was the 24th of May a year later when we played Man United at home and stayed up.
???It???s the 24th of May again this year and we???re playing Man United again at home and our opponents, assuming Sunderland do get the point tonight, will again be Newcastle, our rivals in terms of relegation, who are again playing a side in claret and blue. They were playing Aston Villa in 2009 so there are some omens in Hull City???s favour.
???Clearly the big challenge they have got is that they are two points adrift and it???s not in their own hands. Of course the stats will tell you that Steve Bruce has never beaten Manchester United and it???s going to be a very difficult task.
???Obviously if Louis van Gaal decides to put in a team of Man United youngsters, and no one should ever underestimate Manchester United youngsters, it may be different.???
Duffen said he is expecting a tension-filled KC Stadium on Sunday and doesn???t think playing at home will help either Hull or Newcastle.
He added: ???I think the nerves will be difficult. One of the biggest challenges, I believe, both for Newcastle and Hull City is that they are both playing at home. I don???t think either of those grounds are particularly happy for the home sides at the moment, there???s a lot of pressure coming from the stand and that could add to the tension for everybody.
???From the board room or directors box perspective it???s very difficult because you have little or no influence and I think particularly for Hull City this time around because they are a bit shell-shocked that they are in this position at all.???
Despite the financial implications which come with relegation from the Premier League, Duffen thinks Hull will be in good shape if they are demoted.
However, he pointed at other factors contributing to troubled seasons for relegated teams and said the mood within any club has to be a good one to avoid falling out of the top division.
He added: ???Partly that???s about finances, but I think it is also about momentum and sadly if you look around the Premier League at the moment and you look at clubs of comparable stature and development, ask yourself why West Brom, Swansea, Crystal Palace have had such a successful season and clubs like Newcastle, QPR and Hull City have been struggling.
???I think to the outside observer the three clubs that aren???t doing so well look like troubled clubs and I think that does make a huge difference in the way the club perform.
???It???s not just about money; it???s about the whole atmosphere. It is about the engagement with the fans and the spirit that means you???re a happy camp and that really does help.
???People say the fans can be the 12th man when it is going well; I think they can also mean you???re down to 10 men when it is not going well.
???In terms of finances I think Hull City will be fine. I think the Allam family are very prudent owners and they have supported Steve Bruce magnificently in the transfer market but I???m sure they???ll have the relegation clauses built into player contracts and they???ll be able to re-profile the squad in the event that they do get relegated.???
Meanwhile, Duffen also weighed into the Raheem Sterling debate after reports emerged that the 20-year-old is set to tell Liverpool that he doesn???t want to sign a new contract.
The former Hull chairman told Sky Sports News HQ that his first instinct would be to sell a player who was seemingly being adversely affected by an agent.
He said: ???I think the most disappointing thing for the club, and one has to assume that it is his agent who has chosen to try and play this out in the public domain, no one likes to be held to hostage to fortune.
???My view would be that if Manchester City or any other suitor are genuinely prepared to pay ??35m-40m for Raheem Sterling in this window then I would wish him well and let him go because it is not a matter of proving a point of principle – it is about doing business.
???I think if you???ve got a player who has that attitude and is being influenced by an agent who may be causing him problems and unsettling him then there is no guarantee he???s going to have a good season next year.
???So my instinct would be to say that if you???re going to get fair value for him, let him go, spend the money wisely and recycle it.???