Jason Woolley was drafted 61st overall in 1989 by the Washington Capitals. Woolley had played Junior B hockey with St. Michael's in his hometown Toronto in 1986-87 and 1987-88.
In the fall of 1988, he enrolled at Michigan State University and scored 37 points as a CCHA freshman. In 1989-90, he improved to 48 points and in 1990-91, he was a CCHA First Team All-Star and a NCAA West First Team All-American with 59 points from the blueline. After Michigan State, Wooley suited for Canada's National Team and represented his homeland at the 1992 Olympic Winter Games, helping the club capture a silver medal. Wooley made his NHL debut on April 12, 1992 in a 4-3 win over the New Jersey Devils. The following season, he played 26 games as a rookie and scored two points. In 1993-94, he played ten games and scored his first goal, on October 8 against the Devils' Martin Brodeur.
On February 15, 1995, Woolley signed as a free agent with the Florida Panthers. In 34 games that season, he scored 13 points. In 1995-96, he helped the Panthers reach the playoffs for the first time in team history. He scored eight points in 13 games and helped the Panthers win the Prince of Wales Trophy in the Eastern Conference finals. In the Stanley Cup finals, Woolley and the Panthers lost to the Colorado Avalanche.
In 1996-97, he was traded with Stu Barnes to the Pittsburgh Penguins for Chris Wells. Woolley scored 36 points in 57 games with the Penguins. On September 24, 1997, he was traded to the Buffalo Sabres for a fifth-round draft pick. In 71 games, he scored 35 points and led the team with 21 power-play points. In the playoffs, he helped the Sabres reach the Eastern Conference finals by recording eleven points in 15 games. In the 1998-99 playoffs, he co-led all defencemen with 15 points as the Sabres won the Prince of Wales Trophy. In the finals, they lost to the Dallas Stars in six games.
In 1999-00, Wooley scored 33 points. In the playoffs, he scored two points in five games. In 2000-01, he led team defencemen with three game-winning goals as the Sabres posted its highest win total (46) in 17 years. Wooley went to play parts of two mor seasons in Buffalo before being traded to the Detroit Red Wings in the early stages of the 2002-03 season.