He had only gone through one week of Dolphins training camp before being released, making him available to the Raiders. The Raiders signed Wheatley on August 4, 1999 to help make up for the loss of Zack Crockett who suffered a broken foot. Ironically, Wheatley, the seventeenth overall selection in the 1995 NFL Draft, earned his 1999 roster spot in a battle with Rashaan Salaam, the twenty-first overall selection in the 1995 NFL Draft, who had been Dan Reeves' preferred draft choice in 1995. Wheatley was paired in the Raiders backfield with Napoleon Kaufman, the eighteenth overall selection in the 1995 NFL Draft. While in Oakland, Wheatley would achieve much greater success than he had in New York. Wheatley rushed for 1,000 yards in a season, led the Raiders in rushing three times, appeared in three consecutive playoffs (including one Super Bowl) and finished in the top-10 in the NFL for rushing touchdowns twice. Through the 2007 NFL season, Wheatley was the seventh leading rusher in Oakland Raider history with 3,682 yards as a Raider. In his role as a Raider, Wheatley was able to contribute to some of the greatest memories in the history of the franchise. Seven of his eight career 100-yard rushing games came as a Raider. Five of these games were at the Oakland Coliseum and two were on the road against the Seattle Seahawks. None of these games came in the playoffs where his highest rushing total was 56 yards. Jon Gruden era (1999–2001) How well Wheatley complemented Napoleon Kaufman in Oakland was quickly evident to the New York media, and his newfound success was noticed when the Giants had an impotent running game in his absence. In his early years with the Raiders, Wheatley quickly made good on the promise of his potential with a combination of the power to run inside and the speed to run outside. Wheatley was quite popular in Oakland. The players liked him and his coach, Jon Gruden, even joked with him during his interviews. On the field, Wheatley became an important part of a surprisingly efficient West Coast offense run by Jon Gruden. In 1999, Wheatley was the Raiders' leading rusher and their only running back to have more than one touchdown reception. For the first time, Wheatley had multiple 100-yard games in the same season: 100 yards on 20 rushes on October 3 against the Seattle Seahawks