If you want to talk about the Oakland Raiders vs Chicago Bears rivalry, you have to start with the violence. Forget the "modern" NFL for a second. Put away the clean jersey sales and the fantasy football apps. This series was born from a specific kind of 1970s and 80s grit that basically doesn't exist anymore.
Honestly, it’s a weird matchup. They don't play often. They’re in different conferences. Yet, every time they meet, something bizarre or brutal tends to happen.
The 1984 Bloodbath at Soldier Field
Most fans point to the 2019 "Khalil Mack Bowl" in London as the peak of this series. They're wrong. The real peak—or maybe the valley, depending on how much you like defensive struggles—was November 4, 1984.
The Raiders were the defending Super Bowl champs. The Bears were the "Monsters of the Midway" in the making. It was cold. It was ugly.
Chicago sacked Raiders quarterbacks nine times. Nine. They didn't just win; they shattered the Raiders' mystique of intimidation in a single afternoon. Marc Wilson, the Raiders' QB, played through a broken thumb. Jim McMahon, the Bears' "punky QB," had his season ended by a brutal hit. It was a game that changed how the league looked at physical defense.
People think the "Oakland Raiders vs Chicago Bears" matchup is just another cross-conference game. But that 1984 clash was the moment the torch passed. The Raiders' era of dominance was fading, and the 1985 Bears were being forged in the frozen turf of Soldier Field.
The Khalil Mack Ripple Effect
You can’t talk about these two teams without mentioning the trade that stopped the NFL world in 2018. Jon Gruden shipping Khalil Mack to Chicago was a "where were you" moment.
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Raiders fans were devastated. Bears fans felt like they’d just won the lottery.
When they finally met in London in 2019, the narrative was served on a silver platter. It was the ultimate revenge game. But the Raiders did something nobody expected: they bullied the bullies.
Why the 2019 Game Mattered
- Josh Jacobs announced himself to the world, outperforming the entire Bears' rushing attack.
- The Raiders' offensive line held Mack to zero sacks.
- It proved that a single superstar—even one as transcendent as Mack—can't always overcome a disciplined game plan.
It was a classic "Gruden" win. Heavy sets, power running, and a refusal to let the opponent's best player breathe. Even though Mack is gone from Chicago now, that trade remains the defining lens through which fans view the modern era of this rivalry.
The Recent Heartbreak at Allegiant
Fast forward to the most recent chapter. On September 28, 2025, at Allegiant Stadium, we saw yet another classic. The Raiders (now in Las Vegas, but still carrying that Oakland "Silver and Black" DNA) fell 25-24 to the Bears in a game that felt like a fever dream.
Geno Smith, the Raiders' veteran signal-caller, threw three interceptions. All three were intended for Jakobi Meyers. Tyrique Stevenson and Kevin Byard III looked like they were running the routes for him.
But the Raiders didn't just lie down. Rookie sensation Ashton Jeanty went nuclear, racking up 138 yards on the ground, including a 64-yard house call that made the stadium shake. Maxx Crosby was doing Maxx Crosby things—tipping passes, forcing fumbles, and even snagging an interception of his own off Caleb Williams.
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What Really Happened in the Final Minutes
The ending was pure chaos. Caleb Williams, the Bears' young star, showed why he was the top pick. Down 24-19, he led a 69-yard march that looked effortless. D’Andre Swift punched it in with 1:34 left on the clock.
Raiders kicker Daniel Carlson had a chance for redemption. A 54-yarder to win it. He’s usually money. But Josh Blackwell—a special teams ace most people wouldn't recognize in a grocery store—burst off the edge and blocked it.
Game over.
That loss dropped the Raiders to 1-3 for the season and propelled the Bears to their 800th franchise win. They became only the second team in NFL history to hit that mark, joining the Green Bay Packers.
The Stats Nobody Talks About
Most people assume the Bears have always dominated this series because of their historical "Monster" reputation.
Actually, it’s remarkably close.
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The Bears lead the all-time series 10-8. That’s it. For decades, the Raiders held the edge. Since 2003, however, Chicago has taken three of the last five. It’s a pendulum that swings every few years.
Key Personnel Shifts
The 2024-2025 landscape for the Bears looks wildly different under coach Ben Johnson. They’ve added pieces like Luther Burden III and Colston Loveland. They are built for the modern, fast-paced game.
The Raiders, meanwhile, are leaning into a heavy rushing identity. Between Ashton Jeanty and Dylan Laube, they want to wear you down. It’s a clash of philosophies that mirrors the old AFL vs NFL battles of the 60s.
Actionable Insights for Fans
If you're tracking the Oakland Raiders vs Chicago Bears history for betting, trivia, or just pure fandom, keep these nuances in mind:
- Watch the Trenches: In almost every Raiders-Bears matchup, the team that wins the sack battle wins the game. This isn't a "passing league" rivalry; it's a "defensive line" rivalry.
- The Turnover Bug: Geno Smith’s three-pick performance in 2025 isn't an anomaly. Historically, these teams force each other into mistakes.
- Location Matters: Since 2011, these teams haven't played in the same city twice in a row. They’ve gone from Oakland to Chicago to London to Las Vegas. The "travel fatigue" factor is real.
To stay ahead of the next matchup, you should start by analyzing the Raiders' defensive line depth against the Bears' interior offensive line. The Bears' recent additions of Jonah Jackson and Joe Thuney were specifically designed to stop guys like Maxx Crosby. If the Raiders can't penetrate that middle, Caleb Williams will have all day to find Rome Odunze. Keep an eye on the injury reports for the Raiders' secondary as well, as they've struggled with consistency in high-pressure fourth-quarter situations.