Eldredge began skating when he was five years old and moved from Chatham, Massachusetts, to Philadelphia at age ten to train with Richard Callaghan. He later trained at the Detroit Skating Club in Bloomfield Hills, Michigan and at the Onyx in Rochester Hills, Michigan. He won silver at the 1987 World Junior Championships and then gold in 1988. He took bronze at the 1988 Skate America.
In the 1989–90 season, Eldredge won his first senior national title and was sent to the 1990 World Championships, where he finished fifth. The following season, he repeated as the national champion and then took the bronze medal at the 1991 World Championships. Although Eldredge missed the 1992 U.S. Championships, he was nominated to represent the U.S. at the 1992 Winter Olympics. He placed tenth in Albertville and then seventh at the 1992 World Championships.
Eldredge struggled during the next two seasons, coming sixth at the 1993 U.S. Championships and fourth in 1994, and was not selected for the 1994 Olympics. He regained momentum in the 1994–95 season, taking silver at the 1994 Goodwill Games and gold at the 1994 Skate America and 1994 NHK Trophy. He then won his third national title and silver at the 1995 World Championships. In 1996, he came away with silver at the U.S. Championships but won gold at the 1996 World Championships.

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