Charlie Huddy played two seasons of major Junior A hockey with the Oshawa Generals but was not drafted by any NHL team. During his final year with the Generals, Huddy had 20 goals and 58 points in 64 games.
Huddy joined the CHL's Houston Apollos for the 1979-80 campaign, scoring 14 goals and 48 points in 79 games. The following year, he made it to the NHL for 12 games, suiting up with the Edmonton Oilers. Huddy's play in Edmonton earned him a spot for 41 games the following year, and, by 1982-83, he was patrolling the Oiler defense on a full-time basis. He responded with 20 goals and 57 points in 76 games. That year, the young Oilers advanced all the way to the Stanley Cup finals where they lost to the three-time defending champion New York Islanders. Huddy and the other players were devastated by the defeat but came back even stronger the following season and avenged their loss from the previous year, beating the Islanders in the finals, and denying them their fifth Cup victory in a row. In September 1984, Huddy was selected as a member of Team Canada which won the gold medal at the Canada Cup tournament.
The Oilers and Huddy successfully defended their championship the following year, beating the Philadelphia Flyers in the Cup finals. It's quite likely the team was on pace to win five championships in a row, but an errant pass by fellow defenseman Steve Smith bounced off goalie Grant Fuhr's skates and accidentally slid into the Oiler net during a playoff game against the rival Calgary Flames in 1986. The Oilers were unable to get the equalizer, and the Flames advanced to the Stanley Cup finals, where they eventually lost to the Montreal Canadiens.
Despite not making it to the championship round in 1986, most in the hockey world still felt the Oilers were the best team in the NHL, and with good cause. The team rebounded to win their third championship in four years, once again beating the Philadelphia Flyers in a tough seven-game series. In 1987-88, the Oilers were back in the finals again, this time facing the Boston Bruins, who were unable to keep pace with the speedy Oilers, going down in four-straight games.
During that off-season, Huddy, the Oilers, and hockey fans everywhere were left in a state of shock with the announcement team captain Wayne Gretzky had been traded to the Los Angeles Kings. That year, the club turned in a strong performance, but the Calgary Flames emerged as the best team in the league, winning their first Stanley Cup title.
With the likes of Huddy, Mark Messier, and Jari Kurri still leading the charge, the Oilers re-grouped and won another Stanley Cup in the spring of 1990, once again beating the Boston Bruins, thanks largely to stellar goaltending from Bill Ranford.
Huddy remained with the Oilers for another season before signing with the Los Angeles Kings in 1991-92. He was now re-united with Wayne Gretzky, and the Kings made a push all the way to the Stanley Cup finals in 1993, before falling to the Montreal Canadiens in five games. Huddy remained in L.A. for three years before being moved to the Buffalo Sabres during the shortened 1994-95 season. He had a short 12-game stopover with St. Louis before returning to the Sabres where he played the last game of his NHL career in 1996-97.