In September 1991, Redfearn joined Barnsley, and it was at this club he arguably spent his prime years. In his seven seasons at Oakwell, he rarely missed a single game, and was named club captain and penalty taker. In the 1996–97 season, Redfearn scored 17 goals as Barnsley won promotion to the FA Premier League for the first time in the club's history. Redfearn missed only one game, and was Barnsley's top scorer with ten league goals in the 1997–98 season. These included Barnsley's first ever top division goal on the opening day of the season, when he put them ahead in the ninth minute at home to West Ham United, although they ended up losing the game 2–1.