1960s
- Friday, September 16, 1960The Chiefs, then known as the Dallas Texans, played the Oakland Raiders for the first time at Kezar Stadium in San Francisco, California. The Texans defeated the Raiders, 34-16. Running back Jack Spikes led the way for the Texans with 13 rushing attempts for 88 yards and a touchdown.
- Thursday, September 13, 1962Owner Lamar Hunt traded quarterback Cotton Davidson to Oakland for the Raiders' first-round draft pick in the AFL's 1963 draft along with the negotiating rights to tackle Fred Miller. Hunt made the trade without consulting with head coach Hank Stram and upon learning of the move, Stram was furious. The Texans franchise would use the pick on future Hall of Fame defensive tackle Buck Buchanan.
- Wednesday, June 8, 1966Under leadership from Chiefs owner Lamar Hunt, the AFL agreed to merge with the NFL, much to the dismay of Raiders owner Al Davis, who at the time had been the AFL's commissioner.
- Sunday, January 15, 1967After splitting their season series with the Raiders, the AFL Champion Chiefs played in the first ever Super Bowl. The Chiefs lost to the Packers, 35-10.

- Sunday, January 14, 1968After sweeping the season series with the Chiefs, the AFL Champion Raiders played in the second ever Super Bowl. The Raiders lost to the Packers, 33-14.
- Sunday, December 22, 1968In the 1968 season, the Chiefs and Raiders split their regular season matchups and were both 12-2 entering the AFL's divisional round. The Raiders routed the Chiefs, 41-6, at Oakland-Alameda County Coliseum to advance to the AFL Championship.
The Raiders lost to the Jets, 27-23.

1970s
- Sunday, January 4, 1970Entering the 1969 playoffs, the Chiefs were 11-3 and the Raiders were 12-1-1, including two regular-season wins over the Chiefs. In the playoffs, the Chiefs beat the New York Jets to advance to the AFL Championship versus the Raiders on January 4, 1970.
The Chiefs beat the Raiders in the AFL Championship, 17-7. With the NFL merger taking place the following year, it was the AFL's final game, and the Chiefs advanced to Super Bowl IV.
- Sunday, January 11, 1970The Chiefs won Super Bowl IV by defeating the NFL's Minnesota Vikings, 23-7.

- Sunday, November 1, 1970In a pivotal game against the Raiders, the Chiefs were ahead, 17-14, when quarterback Len Dawson apparently sealed the win when he ran for a first down that would have allowed the Chiefs to run out the clock.
But while on the ground, Dawson was speared by Oakland defensive end Ben Davidson. Kansas City wide receiver Otis Taylor retaliated and a bench-clearing brawl ensued. Offsetting penalties were called, nullifying Dawson's first down.
The Chiefs punted the ball and Raiders kicker George Blanda eventually booted a game-tying field goal with eight seconds remaining. The tie eventually cost the Chiefs the AFC West division crown as Kansas City finished the year with a 7-5-2 record, while the Raiders went 8-4-2.
- Sunday, January 9, 1977The Raiders won Super Bowl XI by defeating the Minnesota Vikings, 32-14.

1980s
- Sunday, January 25, 1981The Raiders won Super Bowl XV by defeating the Philadelphia Eagles, 27-10.
- Sunday, January 22, 1984The Raiders won Super Bowl XVIII by defeating the Washington Redskins, 38-9.
1990s
- Saturday, December 28, 1991The Chiefs defeated the Raiders in the wild card round of the NFL playoffs, 10-6. Running back Barry Word rushed 33 times for 130 yards. The Chiefs won all three contests against the Raiders that season.

- Sunday, November 14, 1993Former Raider Marcus Allen returned to the Los Angeles Memorial Coliseum as a member of the Chiefs and ran for 85 yards on 17 carries and a touchdown in Kansas City's 31-20 victory over the Raiders.
- Monday, February 15, 1999The Oakland Raiders signed former Chiefs quarterback Rich Gannon. Gannon would go on to lead the Raiders to an AFC Championship in the 2002 season.
2000s
- Sunday, October 21, 2007The Chiefs defeated the Raiders, 12-10, for their ninth straight victory against Oakland. Chiefs running back Larry Johnson rushed 24 times for 112 yards and a touchdown in the win.

2010s
- Sunday, October 13, 2013The Chiefs ended the Raiders' six-game winning streak at Arrowhead Stadium with a 24-7 win in a game in which Arrowhead Stadium set the record for the loudest open-air venue at 137.5 decibels.

- Thursday, November 20, 2014The Raiders, who were winless, defeated the Chiefs, 24-20, on Thursday Night Football, snapping Kansas City's five-game winning streak.
The top shots from the Chiefs vs. Raiders series history

RB #34 Bo Jackson breaks for a big run during the Chiefs 24-20 win on November 25, 1990.

Raiders RB Nick Bell is tackled by Chiefs S Deron Cherry and LB Ervin Randle during the Chiefs 10-6 win in the 1991 AFC Wild Card Playoff Game on December 28, 1991

Chiefs LB Derrick Thomas covers Raiders WR Willie Gault during the Chiefs 7-28 loss on December 6, 1992.

Chiefs RB Marcus Allen crosses the goal line for a third quarter touchdown as Raiders' Eddie Anderson tries to stop him during the Chiefs 31-20 win on November 14, 1993.

Chiefs QB Joe Montana prepares to hand off to RB Greg Hill in the second quarter during the Chiefs 19-9 win on December 24, 1994.

Chiefs LB Derrick Thomas runs onto the field as he is introduced to the crowd against the Oakland Raiders during the Chiefs 23-17 win on September 17, 1995.

Chiefs RB Marcus Allen runs for yardage against the Oakland Raiders during the Chiefs 19-3 win on September 8, 1996.

Chiefs QB Rich Gannon scores a touchdown after getting past Raiders defenders James Trapp and Darrell Russell during the Chiefs 30-0 win on December 7, 1997.

Chiefs LB Greg Favors and Raiders Tackle Lincoln Kennedy have a discussion during the Chiefs 31-24 win on December 26, 1998.

TE Mitch Jacoby making a spectacular catch during the Chiefs 37-34 win on November 29, 1999.

Chiefs DT Chester McGlockton tackles Raiders QB Rich Gannon during the Chiefs 49-31 loss on November 5, 2000.

Chiefs DB Greg Wesley dives at Raiders QB Rich Gannon during the Chiefs 28-26 loss on December 9, 2001.

Chiefs TE Tony Gonzalez makes a catch in a steady downpour as Raiders S Derrick Gibson closes in late in the fourth quarter during the Chiefs 24-0 loss December 28, 2002.

Chiefs Kicker Morten Anderson nails a 35-yard field goal with nine seconds left giving the Chiefs a 27-24 win on November 23, 2003.

Chiefs FB Tony Richardson leaps over Raiders CB Charles Woodson during the Chiefs 17-10 win on October 20, 2003

Raiders DT Warren Sapp close on the heels of Chiefs QB Trent Green during the Chiefs 37-24 win on Sunday, December 5, 2004.

Chiefs RB Priest Holmes leaps into the end zone for a touchdown past Raiders LB Danny Clark and CB Charles Woodson during the Chiefs 24-17 win on September 18, 2005.

QB Trent Green drops back for a pass during the Chiefs 17-13 win on November 19, 2006.

The Chiefs Defense provides a big hit during their 12-10 win on October 21, 2007.

WR Dwayne Bowe sheds a tackler and gains extra yards after the catch during the Chiefs 8-23 loss on September 14, 2008.

RB Jamaal Charles breaks free for an electrifying run during the Chiefs 16-10 win on November 15, 2009.

WR Dwayne Bowe makes a Touchdown catch during the Chiefs 20-23 loss on November 7, 2010.

WR Dexter McCluster competes for the ball during the Chiefs 10-31 loss on January 2, 2011.

CB Brandon Flowers breaks up the play during the Chiefs 28-0 win on October 23, 2011.