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Jeff Hackett was drafted 34th overall in the 1987 Entry Draft by the New York Islanders. On December 1, 1988, Jeff made his NHL debut against the Blues. On March 11, he earned his first win against the Devils. He played 13 games that first season with the Islanders and went 4-7-0. In 1990-91, he played 30 games for the Islanders. On May 30, 1991, Jeff was claimed in the Expansion Draft by the San Jose Sharks. In 1991-92, he played 42 games and went 11-27-1 with a 3.84 goals-against average. That year, he was the team's Player of the Year award. The following season, he played 36 games for the Sharks and posted a 3.84 GAA. On July 13, 1993, Jeff was traded to the Chicago Blackhawks for a third-round draft pick. That season, he played 22 games behind goaltending partner Ed Belfour. In the shortened 1994-95 campaign, he played seven games. He then made two appearances (26 minutes) in the playoffs as the Blackhawks reached the Western Conference finals before losing to the Red Wings.
In 1995-96, Jeff went 18-11-4 in 35 games with the Blackhawks and posted four shutouts. The following season, he went 19-18-4 and posted two shutouts. In 1997-98, Jeff took over the starting goaltending duties and went 21-25-11 in 58 games. He also posted eight shutouts on the season.
In 1998-99, Jeff was traded on November 16 with Eric Weinrich, Alain Nasreddine and a fourth-round draft pick to the Montréal Canadiens for Jocelyn Thibault, Dave Manson and Brad Brown. After going 2-6-1 with a 3.78 GAA in ten games with the Blackhawks, Jeff went 24-20-9 with a 2.27 GAA and five shutouts in 53 games with the Canadiens. At year's end, he was presented the team's Molson Cup award. In 1999-2000, Jeff went 23-25-7 and posted a 2.40 GAA and three shutouts. On February 22, he recorded the 20th shutout of his career in a 1-0 blanking of the Coyotes. In 2000-01, he was limited to just 19 games (4-10-2) with the Canadiens because of injuries.
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