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Previewing the NASCAR Cup Series Enjoy Illinois 300 at WWT Raceway
Joe Puetz-Imagn Images

After a stunning playoff-opener for the NASCAR Cup Series at Darlington Raceway, the sport's best drivers are heading to the midwest for the Enjoy Illinois 300 at World Wide Technology Raceway. Sunday will mark the venue's fourth race for the Cup Series, and the first taking place during the NASCAR Playoffs.

Fast Facts: Enjoy Illinois 300 at Gateway

Date: September 7, 2025
Track: World Wide Technology Raceway (Madison, Illinois)
Time: 3:00 p.m. ET
TV: USA Network
Stages: 45/140/240
Defending Winner: Austin Cindric
Entry List: 36 Entries for 40 Spots

Enjoy Illinois 300 Schedule

VIEWING GUIDE: How to Watch The Enjoy Illinois 300 at WWT Raceway

Playoff Defense or Playoff Offense?

Joe Puetz-Imagn Images

The 2025 NASCAR Cup Series Playoffs have gotten underway, and for some drivers, after a tough showing in the Cook Out Southern 500 at Darlington Raceway, it's put them on defense heading into the final two races of the 'Round of 16'.

Joey Logano currently sits below the cutline heading to WWT Raceway, a track that both he and Team Penske have excelled at over the last four years. However, the defending champion needs to be on offense this weekend, so that he can avoid being on defense come Bristol -- the track that eliminated him from championship contention in 2023.

Shane van Gisbergen on the other hand; he's on defense. The Auckland, New Zealand-native started the round with 22 Playoff Points and a solid advantage over the cutline, but after a dismal Darlington, the No. 88 is only three points above the cutline -- and going to two racetracks that he's either never seen before, or had a hard time with.

Chase Elliott (+9), Christopher Bell (+11), and Austin Cindric (+12) are also close the cutline heading into the final two races of the first round, and this weekend's event at WWT Raceway could be important to continuing their post-season journey.

Can Kyle Busch End The Winless Drought?

Joe Puetz-Imagn Images

Kyle Busch isn’t one of the 16 drivers in the NASCAR Cup Series Playoffs this season, but the Richard Childress Racing driver is hungrier than ever to make it back to Victory Lane at NASCAR’s top-level.

This weekend, the two-time NASCAR Cup Series champion will return to the site of his most-recent victory in the Cup Series, World Wide Technology Raceway, as the No. 8 Rebel Bourbon Chevrolet looks to return to Victory Lane for the first time in two years.

Busch led a race-high 121 laps in the second running of the Enjoy Illinois 300 Presented by TicketSmarter, securing a dominant win: the 63rd of his NASCAR Cup Series career and the third for Richard Childress Racing.

Since that day in June 2023, the Las Vegas, Nevada-native has had several near-misses and second-place finishes, as one of the most dominant drivers of the 2010s looks to rekindle the spark that made him one of the greatest drivers to compete in NASCAR.

Busch will return to Richard Childress Racing in 2026, after signing a one-year contract extension with the organization. Hopefully, when the season starts next year, though, the winless streak has already been snapped.

Hendrick Motorsports in Trouble?

Logan Reily, Getty Images

For Hendrick Motorsports, the dismal results of last weekend's Cook Out Southern 500 at Darlington Raceway were... confusing, especially for a team that has thrived at the 1.366-mile egg-shaped oval in the past.

None of the organization's four playoff-eligible drivers finished inside the top-15 at Darlington, with the best of the four being Chase Elliott in 17th. So, is there concern within the Hendrick Motorsports camp? There has to be, right?

Maybe more concerning for the 14-time championship-winning organization, though, is that none of the team's four drivers have particularly stellar results at World Wide Technology Raceway.

Chase Elliott and Alex Bowman, the two drivers from Hendrick Motorsports in the worst position when it comes to the cutline, have not finished inside the top-10 at World Wide Technology Raceway in three starts -- and have average finishes of 17.0 (Elliott) and 22.3 (Bowman). Kyle Larson has one top-five and two top-10s at the track, while William Byron has only a single top-10 and an average finish of 14.0.

Could another subpar weekend be on the cards for Hendrick Motorsports at WWT Raceway, and how could that impact the organization's aspirations to place all four entries into the Round of 12?

This article first appeared on Racing America on SI and was syndicated with permission.

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