In 1991, Waltrip and Hammond formed Darrell Waltrip Motorsports, where the combination clicked again, but in mid-1992, Hammond left after a win at Pocono Raceway when SABCO Racing owner Felix Sabates named him to work with Kenny Wallace for the 1993 season. Hammond teamed up again with Waltrip in 1996, but the two were unable to recapture the magic of the 1980s. In 1998, Hammond joined Roush Racing as crew chief for Chad Little. The combination was an immediate success. Despite failing to qualify for the spring race at Atlanta Motor Speedway, Little finished second at the Texas 500 and had a career high 15th place in the championship standings. Hammond stayed with Roush Racing until the end of the 2000 season; this included a stint where he was crew chief for Kurt Busch for the first six races, before leaving after he was hired to work at Fox Sports.