Manny Ramirez is considered the most highly rated player to wear 99.
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Jersey #99 was retired league wide when Wayne Gretzky retired, therefore no one else has had that number since he wore it. However, there were other players who wore that number before him, and probably other players on other teams that wore the #99 at the same time that he wore it for his team.
The number 86 is the only number left in the NHL between 00-99 that has never been used. Edit: The answer above is wrong. Every single number between 00-99 has been worn. The last number that wasn't worn was 84, which Guillaume Latendresse wore with the Canadiens. Mikael Grabovski wears it with the Maple Leafs currently. There have been 3 players who have worn the number 86: Jonathan Ferland for the Canadiens in 2006, Jeremy Williams for the Rangers in 2011 and Wojtek Wolski for the Phoenix Coyotes and New York Rangers currently.
Paul Gascoigne Dwight Yorke Frederic Kanoute
Joe Lamb (Montreal Canadiens 1934-35), Wilf Paiement (Toronto Maple Leafs 1979-82), and Rick Dudley (Winnipeg Jets 1980-81) also worn that number. However, no players have donned that number since Gretzky's 99 was retired league-wide in 2000.
They can wear from 0-99, Major League Baseball won't issue uniforms that have triple digit numbers.