Jason Woolley was drafted 61st overall in the 1989 Entry Draft by the Washington Capitals. After the 1992 Winter Olympics, Jason made his NHL debut on April 12 in a 4-3 win over the Devils. The following season, Jason 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, Jason signed as a free agent with the Florida Panthers. In 34 games that season, he scored 13 points. In 1995-96, Jason helped the Panthers reach the playoffs for the first time in team history.
His 34 points that season ranked second amongst team defencemen. In the playoffs, 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, Jason and the Panthers lost to the Avalanche.

In 1996-97, Jason was traded on November 19 with Stu Barnes to the Pittsburgh Penguins for Chris Wells. Jason scored 36 points in 57 games with the Penguins. On September 24, 1997, Jason was traded to the Buffalo Sabres for a fifth-round draft pick. In 71 games, Jason scored 35 points and led the team with 21 power-play points. In the playoffs, he helped the Sabres reach the Eastern Conference finals with 11 points in 15 games. In 1998-99, Jason averaged 18:43 minutes of ice time per game and scored a career high 10 goals, 33 assists and 43 points. In the playoffs, Jason co-led all defencemen with 15 points as the Sabres won the Prince of Wales Trophy. In the finals, they lost to the Stars in six games.

In 1999-2000, Jason scored 33 points and averaged 17:51 minutes per game. In the playoffs, he scored two points in five games. In 2000-01, Jason led team defencemen with three game-winning goals as the Sabres posted its highest win total (46) in 17 years. In 2001-02, Jason was limited to 59 games but still finished second amongst Sabres¹ defenceman with 28 points.

In 2002-03, Jason was traded to the Detroit Red Wings on November 16 for future considerations. After scoring three points in 14 games with the Sabres, he scored 23 points in 62 games with the Red Wings and helped his new team win the Central Division title. On February 13, in his first game against the Sabres, he scored a goal in a 4-2 victory. In the playoffs, Jason scored one goal in four games as the team lost in the opening round to the Mighty Ducks.

In 2003-04, Jason was traded on Nov. 16 to the Detroit Red Wings for future considerations. Jason scored 19 points in 55 games as he helped his new team win the Presidents¹ Trophy with the best record in the league. In the playoffs, the Red Wings reached the second round before losing to the Flames.

Currently, Jason played with Detroit for 05 and in the Swedish Elite League 06. Only this year has he taken a break.