I think former rep. Gary Franks(R) of Connecticut the same scenario happened. He won 3 way races in 1990 and 1992 and beat James Maloney in 1994 I think and his luck ran out in 1996 and he lost in a re-match to Maloney. His district was conservative back in the day to what you think of it nowadays. The district has moved left of center. Of course the 5th district does include the old 6th district too which it didn't back in the 1990's/early 2000's.
Speaking of Connecticut, Sam Gejdenson (D-CT-02) won by only
21 votes in 1994 (and had had what
Wikipedia describes as very close races in 1982 and 1992 (against the same opponent as in 1994 I know) as well) before losing in 2000.
