In the June 23, 1995, Davis signed a letter of intent to move the Raiders to Oakland after. The move was approved by the Alameda County Supervisors table the following month, also for the NFL. The move was greeted with much fanfare, and under new head coach Mike White the 1995 season started well for the team. Oakland started 8-2, but injuries to starting field marshal Jeff Hostetler contributed to a six-game series loss to end the season and the Raiders failed to qualify for the finals for a second consecutive season.
After three unsuccessful seasons under White and his successor, Joe Bugel, Davis selected a new head coach from outside the Raiders organization for only the second time when the employment of Philadelphia Eagles offensive coordinator Jon Gruden, who worked previously for the 49’s and packaged under head coach Mike Holmgren. Under Gruden, the Raiders posted consecutive 8-8 seasons in 1998 and 1999 and left last place in the AFC West. Oakland finished 12-4 in 2000, the most successful team in a decade. Directed field marshal veteran Rich Gannon, Oakland won their first division title since 1990 and advanced to the AFC Championship, where they lost 16-3 to the eventual Super Bowl champion Baltimore Ravens.
The Raiders acquired receiver Jerry Rice before the 2001 season. They finished 10-6 and won a second straight AFC West title but lost their divisional-round game to end the New England Patriots of the eventual Super Bowl champion in a controversial game that became known as “The Tuck” . The game was played in a heavy snowstorm, and late in the fourth quarter of an apparent loose ball field marshal Patriots Tom B was recovered by Raiders Greg Biekert supportive. The recovery would have led to a Raiders victory, but the scheme was reviewed and was determined to be an incomplete pass (it was ruled that B had pump falsified and then “got” the ball into his body in which, by the rule, may result in a blunder). The Patriots retained possession of the ball and ran for a field goal game-winner. The game went further and the Patriots won, 16-13.
Shortly after the season, the Raiders made an exceptional move that involved releasing Gruden from his contract and allow the Tampa Bay Buccaneers to sign it. In return, the Raiders received cash and future draft the pickings of the Buccaneers. The sudden move came after months of speculation in the media that Davis and Gruden had fallen personally and professionally. Bill Callahan, who served as offensive coordinator of the team and offensive line coach during Gruden of the occupation, were named to head coach.
By Callahan the Raiders finished the 2002 season 11-5, won their third straight title in the division and clinch the first seed in the playoffs. Rich Gannon was named MVP of the NFL after going to a league-high 4689 yards. After winning the New York Jets and Tennessee Titans by large margins in the playoffs, the Raiders made an appearance in Super Bowl XXXVII. His opponent was the Tampa Bay Buccaneers, coached by Gruden. The Raiders, who had not made significant changes to Gruden offensive schemes, were intercepted five times by the Buccaneers to a 48-21 route of higher. Some Tampa Bay players claimed that Gruden had given much information on the Oakland offense, they knew exactly what they were called schemas.
Callahan second season as head coach was considerably less successful. Oakland finished 4-12, their worst acting since 1997. After a loss of late-season the Denver Broncos, a visibly frustrated Callahan exclaimed, “We must be the dumbest team in America in terms of playing the game.” at the end of the 2003 regular season Callahan was fired and was replaced by former Washington Red Skins head coach Turner Norvo.
The team’s fortunes did not improve in Turner’s first year. Oakland finished the 2004 season 5-11, with only one divisional win (a one-point victory over the Broncos in Denver). During a Week 3 victory against the Buccaneers, Rich Gannon suffered a neck injury that ended his season. He never returned to the team and retire before the 2005 season. Kerry Collins, who led the New York Giants to an appearance in Super Bowl XXXV and signed with Oakland after the 2003 season, became the team begins to field marshal.
In an effort to strengthen its offense, in early 2005 the Raiders acquired Pro Bowl receiver Randy Moss via open trade with the Minnesota Vikings, and became runner LaMont Jordan of the New York Jets.