This was the only year I watched the Cup races. I distinctly recall Mighty Mary making a tactical error against Stars and Stripes going back up course to help lose that 4:08 last leg lead. I cant find any video about the maneuver, but I would love to see that somewhere online, the path during the last leg illustrated should be available somewhere. We will never know how many races Mighty Mary might have won if they went up against NZ.
"In the key maneuver, Mighty Mary sailed into a windless hole on on the right side of the course just when the mostly female team thought it had knocked Conner out of the three-boat final series to select a defender. Within a quarter-mile of the finish in its do-or-die match, Mighty Mary lost the momentum that had allowed it to lead Stars & Stripes around the course. Conner sailed to the left, and his dark blue boat caught more wind than Mighty Mary in a southwest breeze that was dying to less than 4 knots. It was a tactical error for Mighty Mary. As the lead boat, Mighty Mary should have covered Stars & Stripes by staying in the same wind pattern. When the yachts finally came together, the lead had gone from about 40 boat lengths to less than 3. Stars & Stripes rolled past Mighty Mary, but minutes later, Conner's boat ripped out a gennaker sail. In a heart-stopping maneuver, Conner's crew got another sail up in time to hold off Mighty Mary at the finish, where Stars & Stripes crossed with only three boat lengths to spare." www.nytimes.com/1995/04/27/sports/yacht-racing-conner-rides-the-wind-past-mighty-mary-to-gain-finals.html
Your answer is at 1:18:15 - first rule of match racing, always cover your opponent and put your boat between and the mark. I am sure that decision haunts the entire crew to this day, knowing that blew it and therefor their chance to sail the America's Cup. This is same issue that cost Conner the 1983 Cup.