The 2026 NASCAR Cup Series season has produced plenty of surprises through 18 races.
Toyota has won 11 events. Denny Hamlin and Tyler Reddick have spent much of the summer battling atop the standings. Ty Gibbs has emerged as a legitimate championship contender. Meanwhile, several drivers have already punched their tickets to the Chase.
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But perhaps the biggest surprise is who’s still missing from Victory Lane.
Three former NASCAR Cup Series champions, drivers who own a combined six championships and 105 career Cup victories, are still searching for their first win of the season heading into Sunday’s return to Chicagoland Speedway.
While each remains mathematically in the title picture, the pressure to break through only grows as the regular season enters its second half.
Kyle Larson has the speed, but not the wins
If there is one driver on this list who feels closest to a breakthrough, it’s Kyle Larson.
The Hendrick Motorsports star sits fifth in the Cup Series standings with 571 points despite never reaching Victory Lane this season. Larson has collected eight top-five finishes and 11 top 10s, numbers that typically belong to a driver with multiple trophies by this point in the year.
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Instead, he’s repeatedly found himself close without closing the deal.
Larson has remained one of the fastest drivers in the series on intermediate tracks, making Chicagoland an intriguing opportunity. He also tested at the 1.5-mile oval earlier this spring, giving him valuable experience before NASCAR’s first race there since 2019.
Given his week-to-week speed, few would be surprised if Larson is the first driver on this list to end his drought.
Joey Logano’s title defense has taken an unexpected turn
Few expected the three-time Cup Series champion to spend July still looking for his first victory.
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Yet that’s exactly where Joey Logano finds himself.
The Team Penske driver enters Chicagoland 20th in the standings with 370 points after an inconsistent first half of the season. Logano has recorded two top-five finishes and five top 10s, but the dominant performances that have defined many of his championship runs simply haven’t materialized.
That’s especially notable considering Logano has built a reputation for peaking at the right time.
With the Chase still months away, there is no reason to panic. Still, another winless weekend would only increase the attention surrounding one of the sport’s biggest names.
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Brad Keselowski is still trying to complete RFK Racing’s turnaround
Brad Keselowski’s season has looked far more competitive than his stat line might initially suggest.
The RFK Racing co-owner enters Chicagoland 18th in points with 376, backed by two top-five finishes and four top 10s. More importantly, RFK Racing has shown steady improvement as the season has progressed, regularly placing its cars inside the top 10 on speed.
Keselowski has also remained heavily involved in the organization’s long-term growth, recently discussing how manufacturers can better collaborate behind the scenes to compete with Toyota’s current advantage.
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Now, the next step is obvious.
Turning improved speed into a trip to Victory Lane.
A win would not only end Keselowski’s personal drought but also provide another milestone in RFK Racing’s continued resurgence.
Chicagoland could change the conversation
The return to Chicagoland Speedway creates one of the more unpredictable weekends of the season.
The track hasn’t hosted a Cup Series race since 2019, meaning teams are working with limited recent data despite preseason testing. That uncertainty could create opportunities for experienced veterans who have succeeded there before.
Larson, Logano and Keselowski have all proven they know how to win championships.
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Now they’re chasing something much smaller, but perhaps just as important at this stage of the season: a single victory that could completely reshape the narrative of their 2026 campaign before the Chase begins.
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