Bears' Caleb Williams Faces Brutal 2026 QB Duels With Josh Allen, Love and Goff

The Chicago Bears' 2026 schedule is out now, and while it may be the NFL's hardest schedule in terms of last year's winning records, they do have a historic rest advantage that few teams ever get. That should come as a big sigh of relief for quarterback Caleb Williams, who faces new pressures in 2026 following his breakout 2025 season. In as many as seven of the Bears' upcoming games, depending on who starts at quarterback for Minnesota, Williams will be dueling a former first-overall draft pick. That's not even including the former MVP that Williams will face late in the season.

Which of these quarterbacks will give Williams his hardest tests? Let's take a look.

1. Josh Allen - Week 15

It doesn't get much tougher than this. In Week 15, right when the final playoff push begins, Williams will have to travel to the Buffalo Bills' new stadium and square off with the 2024 MVP in prime time on Saturday night. This could be one of the best quarterback duels of the season, as both Williams and Allen have a penchant for making impossible throws look routine. Football fans everywhere will be rooting for this Week 15 matchup to be a Super Bowl preview, especially after one of the most boring Super Bowls in recent memory in 2025.

2. Jordan Love - Weeks 5 and 16

If the last two years are any indication, the biannual duels between Caleb Williams and Jordan Love are going to be must-see TV for the next ten years or more. All five of their meetings have been one-score affairs, with four of the five being decided on the very last play of the game. The 2026 season brings a new wrinkle into this rivalry, as the Bears and Packers will meet on Christmas Day for just the third time in the history of this rivalry, giving the Bears another way to take a 2-1 lead over the Packers.

3. Jared Goff - Weeks 12 and 17

While he lacks the kind of explosive, highlight-reel throws that Williams and Love regularly trade, Goff has been quietly one of the better quarterbacks in the NFL over the past four years. The five-time Pro Bowler and former first-overall pick has thus far gotten the better of Williams in four matchups, but that feels likely to change in 2026. After getting swept by his former team in 2025, including a blowout loss in Week 2, you can bet on Bears head coach Ben Johnson to draw up a diabolical game plan for his quarterback to execute.

4. Trevor Lawrence - Week 13

Williams and Lawrence have only faced off once before, and that was in London in Week 6 of the 2024 season. In that game, Williams had the best performance yet in his NFL career, throwing four touchdowns and earning an elite 90.8 QBR. Lawrence had a much worse time, tossing only two touchdowns for a pedestrian 57.8 QBR. But both quarterbacks are in different situations in 2026 with new head coaches and a better team around them.

In fact, if the 2026 season goes well for both teams, there's a very real chance that this will be a Super Bowl preview.

5. Drake Maye - Week 7

Jacob Martin and Drake May — Chicago Bears DE Jacob Martin sacks New England Patriots QB Drake Maye. Mandatory Credit: Mike Dinovo-Imagn Images | Mike Dinovo-Imagn Images

Whenever two or more quarterbacks are selected near the top of the draft, their careers become inextricably linked. That's what we have here with Caleb Williams and Drake Maye. Both quarterbacks are also coming off a wildly successful 2025 season, with Maye making a Super Bowl appearance and Williams proving that he is the Iceman after making the wildest throw of the year and nearly sending the Bears to the NFC Championship game.

It should come as no surprise, then, that the NFL scheduled these two exciting young quarterbacks for a prime-time matchup in Week 7. This will likely be one of the best Thursday night games of the season as both quarterbacks seek to prove to their fans that 2025 was no fluke.

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