But without that transfer to Tottenham Hotspur, the club’s promotion push under George Burley may have looked very different.
Speaking to Football Presse, Sheepshanks explained that the decision was driven by financial pressure rather than football ambition.
In November 1997, Ipswich Town were flying at the top of the table but still operating with limited resources.
"We were top of the table and we were flying," he recalled. "But as ever, we had no money and we lived on a bank overdraft.
"The bank manager said, 'you have to reduce your overdraft.'"
The club had to raise funds, and reluctantly Sheepshanks and Burley examined which player could be sold without damaging the team's chances.
"George and I sat down with the board and went through all the options. Very reluctantly, we thought Mauricio was the player whose loss would least damage the team."
Taricco was sold to Tottenham for around £1.5 million, a significant fee for a defender at the time. But Sheepshanks had negotiated one important condition.
"I asked David Pleat, 'Can we keep him? We've got two home games this weekend.'
"Can we do the deal with you next week?"
Tottenham agreed. Then came the nightmare scenario. During Ipswich's match against Wolves, Taricco suffered a serious injury late in the game.
"My face went ashen white," Sheepshanks admitted. "Nobody knew what was going to happen.
"I'm thinking, what am I going to do now?"
The transfer appeared to be in danger. However, Pleat stood by his word.
"David Pleat was wonderful.
"They did a medical assessment and agreed they would still go ahead with it because it wasn't going to be a career-ending injury."
The deal was completed, with Tottenham paying half the fee immediately and the remainder later. For Sheepshanks, it was a reminder of the unpredictable nature of running a football club.
"This is life being a chairman."
Taricco's departure was painful, but it allowed Ipswich to strengthen elsewhere and continue their pursuit of promotion. Within a few years, Burley's side reached the Premier League and finished fifth in the top flight.
Looking back, Sheepshanks has no doubt about Taricco's importance.
"He was my favourite. He was one of all our favourites."
And while selling him was difficult, the decision became another example of the fine margins that shaped Ipswich's journey back to the top.