During the 1991-92 season, Wregget was traded to the Penguins as part of the deal that brought Rick Tocchet to the Pens. The Penguins had a rotation of several goaltenders at the time, so he didn’t get much of an opportunity to perform until the 92-93 season. From that point until the 97-98 season, Wregget was the backup for Tom Barrasso, providing reliable and capable relief for the Hall of Fame goaltender. In 94-95 when Barrasso was injured, Wregget played his best hockey, going 25-9-2 and leading the NHL in wins during the lockout-shortened season.

His brightest moment came in the 1995-96 playoffs, when the Penguins were trailing the Capitals one win to two in a best of seven series. Part way through game four, Barrasso left the game with back spams. Wregget stepped in, eventually winning a quadruple overtime marathon that included stopping the first overtime penalty shot in league history. From there Wregget was the hot hand, going 7-1 with a .930 sv%, helping the Pens push past the Caps and Rangers to the conference finals. He’d take the loss in game one against the Florida Panthers before being replaced with Barrasso for the remainder of the series. That move would be questioned by many, as the Pens fell in seven games to the underdog Panthers.

The jersey is littered with puck and stick marks, post paint, one hole, and fairly roughed up crest. It is video matched to the Caps series and photo matched to the Rangers and Panthers series.