Sheppard was selected 60th overall by the Buffalo Sabres in the 1984 NHL Entry Draft. He played 817 career NHL games, scoring 357 goals and 300 assists for 657 points. His best season statistically was the 1993–94 season when he scored 52 goals and 93 points for the Detroit Red Wings. He also played for the New York Rangers, San Jose Sharks, Florida Panthers, and the Carolina Hurricanes. On March 21, 1996, Sheppard scored the first home ice hat trick in Panthers franchise history.
He achieved a rare feat during his career, scoring at least twenty goals in a season for six different NHL teams (accomplishing it in 1999). This was a record of until Bill Guerin passed him by scoring twenty goals with seven teams.
Sheppard has been named the second-best golfer amongst athletes (of sports other than golf) by Golf Digest. He currently serves on the board of directors for the Panthers Alumni Association.

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