Sheepshanks grew up a massive Ipswich fan during the club's halcyon days of the 60s, 70s and early 80s before becoming a director in 1987. He was promoted to chairman in 1995 and subsequently had a rollercoaster 14 years at the helm, that period containing repeated play-off heartache, promotion at Wembley, an incredible fifth-place top flight finish, two stints in the UEFA Cup, relegation and administration.
All of the above is reflected upon in his new book of memoirs - Man on a Mission: The Agony and Ecstasy of a Life in Football. However, the 73-year-old, currently recovering from bowel cancer, is just as keen to look forwards as he is back.
David Sheepshanks celebrates Ipswich Town's promotion to the Premier League in 2000.David Sheepshanks celebrates Ipswich Town's promotion to the Premier League in 2000.
With Ipswich now preparing for what will be the club's second Premier League campaign in 25 years, he enthused: “I'm a Suffolk man, an Ipswich man and I bleed blue and white - I have done ever since being taken to my first game in 1966.
"So seeing how the club is now thrills me. I'm still a fan. I read the news avidly. I still get the same excitement and buzz going to every game.
“I look back and I think that, in 2001/02, had we not suffered that relegation, we would have gone on to do what the likes of Brighton, Bournemouth and Brentford are doing now. But we were, and we paid the price financially.
“It's different now. When these guys were relegated a year ago, of course, everyone was really disappointed, but it was almost as though it was an inconvenience. They were still able to go out and buy a huge number of players and back Kieran (McKenna) and create a team that could get promoted again. Hats off to them because it's unbelievably bloody hard to bounce back like that."
Ipswich Town are gearing up for another season in the Premier League following promotion from the Championship. (Image: PA)
Sheepshanks struggled to find a buyer for Ipswich Town back in the 2000s before eventually selling to Marcus Evans in 2009. The latter, after taking the club down to League One following a lengthy period of stagnation, subsequently sold to the American 'Gamechanger' group in 2021 and a remarkable rebirth followed.
"I think Ipswich can be anything. I absolutely believe that we can," insists Sheepshanks.
"I told Mark (Ashton) when he first came to Ipswich that this is a very special club and that there's not another club in the land like it. There are some other clubs we can look to for inspiration though.
"I can remember when Brighton were several divisions below us. What's been achieved there is a great template and a great exemplar for what we can do. What's been achieved at Brentford and Bournemouth is even more remarkable.
David Sheepshanks was chairman when Ipswich Town had two European campaigns in the early 2000s, including a two-legged tie against Inter Milan.David Sheepshanks was chairman when Ipswich Town had two European campaigns in the early 2000s, including a two-legged tie against Inter Milan.
"So I see no reason why, with the right firm hands on the tiller, we can't aspire to be playing in Europe again. I'm not going to say next year, because that would be too quick."
He continues: "You could say that two years ago, rapidly rising from League One to the Premier League, it was too much too quick for the whole organisation. But this time, I don't think it will be.
"You've got to build and build and build from solid foundations. And the club’s doing that with investment in the academy, in the first team training ground, in the women's team, in the stadium, in the infrastructure and with much more to come no doubt. These are hopefully building blocks for establishing Ipswich Town as a major player in the Premier League.
"Are we as big as the likes of Manchester United, Manchester City, Arsenal, Tottenham etcetera? No, we're not. But can we play with them at the top level? Yes, we absolutely can.
"If we continue to build on solid ground with the right people, and maintain our humility and our special values that exist around this club, then I believe we can go far. There's no limit, really."
Gary O'Neil has stated he is '100% sure' that he will keep Ipswich Town at the top table.New manager Gary O'Neil has stated he is '100% sure' that he will keep Ipswich Town at the top table. (Image: Ross Halls)
Sheepshanks adds: "I've met many of the American owners and they're very passionate. They really love the club. They might not be steeped in it as we are, but the game has changed. Board rooms don’t look like they did in my day. It’s a new world. But ask any of the fans at Portman Road on the 22nd of August if they mind. No, they don’t. They just want to see their team win.
"I hope everyone will get right behind Gary O’Neil and support him and Mark and everybody at the club. Because I think together we can do great things."
Brazilian striker Emersonn arrived from French club Toulouse for a club record fee of £24m last week. He is set to be the first of many signings from across the globe this summer as Ipswich look to be build a squad capable of competing with the best.
David Sheepshanks (right) pictured with Ipswich Town legend Sir Bobby Robson in 2008. (Image: Ashley Pickering)
Sheepshanks reflects: "Back in 2001, after Richard Wright left, we were trying to buy a goalkeeper at the last minute and George (Burley) chose Matteo Sereni on good advice from Tord Grip, who was (England manager) Sven-Goran Eriksson's number two. Finidi George came in too. In hindsight, we began to bring in players who were culturally not the right fit for the club.
"The club faces a similar challenge today. Yes, you need players of the right physicality and strength for the modern Premier League. But you also need the right people. They'll be that much more sophisticated and better at it than we were though, I'm absolutely certain."
Man on a Mission: The Agony and Ecstacy of a Life in Football is available to buy now.
David Sheepshanks' book - Man on a Mission: The Agony and Ecstasy of a Life in Football is out now. (Image: Pitch Publishing)