A NASCAR Cup Series entry list for a race other than the Daytona 500 featuring more than 40 cars is a rarity. In fact, it hadn't happened since the November 2018 race at Texas Motor Speedway, when one driver failed to qualify.
But one week after the field was full at Atlanta Motor Speedway (with no failures to qualify), it has happened this weekend, as there are 41 cars on the entry list for this Sunday afternoon's 75-lap Grant Park 165 around the 12-turn, 2.2-mile (3.541-kilometer) Chicago Street Course in Chicago, Illinois.
With Cup Series races limited to 40 cars, one driver will ultimately fail to qualify for Sunday's race, the one and only street race on the 2025 schedule, and thus become the first driver to fail to qualify for a Cup race other than the Daytona 500 since Timmy Hill at Texas seven seasons ago.
One NASCAR Cup Series driver won't compete in Chicago
The five drivers battling for four spots include Will Brown, who is set to drive the No. 13 Kaulig Racing Chevrolet; Austin Hill, who is set to drive the No. 33 Richard Childress Racing Chevrolet; Josh Bilicki, who is set to drive the No. 66 Garage 66 Ford; Corey Heim, who is set to drive the No. 67 23XI Racing Toyota; and Katherine Legge, who is set to drive the No. 78 Live Fast Motorsports Chevrolet.
The slowest of these five drivers in Saturday's qualifying session will not get to compete on Sunday, regardless of where they stack up against the drivers of the 36 chartered cars, since those entries are all locked into the field.
Given the pace of Kaulig Racing on road and street courses and the overall advantage 23XI Racing and Richard Childress Racing, two other teams that run multiple full-time entries, should have over the part-time teams of Garage 66 and Live Fast Motorsports, odds are the battle for the 40th and final spot in the race will come down to Bilicki and Legge.
And for whatever it's worth, when Hill failed to qualify at Texas in 2018, he was driving for MBM Motorsports, the team now known as Garage 66.
Tune in to TNT Sports this Sunday, July 6 at 2:00 p.m. ET for the live broadcast of the Grant Park 165 from the Chicago Street Course.