After Ray Sheppard was selected by the Buffalo Sabres in the 1984 Entry Draft, he and his agent decided not to sign a contract in order to stay in junior and improve with his OHL team, the Cornwall Royals. It almost didn't pay off. The next season saw his production and games played drop considerably. Talk of a contract still loomed, but this season was not what Sheppard knew he was capable of. For 1985-86, he focused on his specialty?scoring goals. He led the OHL that season in goals with 81 and points with 142. By season's end, he was awarded the Red Tilson trophy as the league's most valuable player. Now he could talk contract with the Sabres.
Sheppard began his NHL career in the 1987-88 season in Buffalo, where he played three seasons. His first season saw him collect 65 points and earn NHL all-rookie team honours. The Sabres traded him to the New York Rangers in 1990 where he played just one season before signing as a free agent with the Detroit Red Wings. It was in "Hockey Town" where he enjoyed his most success. During the 1993-94 season, he had career highs in goals (52), assists (41), and points (93), in 82 games.
Sheppard was on the move once again in 1995 when the Red Wings traded him to the San Jose Sharks for Igor Larionov. During the same season, he was traded once again as the Sharks sent him to the Florida Panthers, a team looking to bolster its offence for their first playoff appearance in club history. With Sheppard's help, the Panthers make it to the Stanley Cup finals against the Colorado Avalanche, only to be swept in four straight games.
Sheppard stayed in Florida for the next few seasons before being traded to the Carolina Hurricanes for the 1998-99 season. He later headed back to the Panthers for the last two seasons and retired in 2001 with 657 career points.