NASCAR Cup Series’ In-Season Tournament Preview: Chicagoland Round 2

The NASCAR Cup Series enters Chicagoland for the first time in seven years with the second round of the In-Season Tournament.

16 drivers won their matchups to stay alive for the million dollars. But, some of the favorites are already gone.

The opening round of the In-Season Tournament at Sonoma Raceway saw a few upsets which included Bubba Wallace, Daniel Suarez, and the No. 1 seeded Tyler Reddick.

Now, eight matchups will take place at Chicagoland for the right to continue on to the third round. Let’s have a look at the matchups below.

32. Bowman vs 16. Cindric

Alex Bowman didn’t just have luck along against Tyler Reddick at Sonoma. He earned his spot into the next round with his third top ten of the season.

Now, he faces Austin Cindric who narrowly outpaced Brad Keselowski to advance.

Cindric has slightly outran his opponent at similar intermediates this season.

This matchup will be close, but Bowman comes into the weekend as the defending race winner.

The Cup Series returns to Chicagoland after seven years and the driver of the No. 48 might have the momentum to slide into the third round.

25. Gilliland vs 9. Hocevar

Todd Gilliland pulled off the upset after his opponent Daniel Suarez had a tough weekend in wine country. He will face another Spire Motorsports standout in the second round.

Carson Hocevar will come into the second round as the favorite in this matchup.

Hocevar comes into the matchup with the clear edge on intermediates and has finished higher than Gilliland in every race but three this season.

Should Hocevar’s current run of races without a DNF continue, he should be through to EchoPark Speedway in Atlanta.

12. Briscoe vs 5. Gibbs

Ty Gibbs and Chase Briscoe make the first of two teammate matchups of the second round.

The Joe Gibbs Racing Toyota teammates both preform well at intermediates so it will be a true battle for the both of them.

Then, both drivers come off strong performances at Sonoma which further solidifies the matchup’s strength.

Chicagoland is also the sister track to Kansas Speedway where Briscoe came out third over Gibbs’ eighth place and that’s where the edge lies.

20. McDowell vs 4. Elliott

Chase Elliott returns to an intermediate against Michael McDowell for their second-round matchup in the ISC.

McDowell is fresh off a fourth top ten on a road course after his ninth place Sonoma run. Unfortunately, his road prowess has not transferred over to intermediates where his opponent has shined in 2026.

If Elliott can continue to run near the front and finish there, he should be able to return to EchoPark Speedway with a shot to further advance and even defend his win.

2. Hamlin vs 15. Jones

Denny Hamlin is now 1-1 against Ty Dillon in the In-Season Challenge! He looked primed to lose the bout once again after his spin at Sonoma resulted in splitter damage. But, Dillon ran into his own problems when he lost power during the final stretch of the race and gave Hamlin the win.

He will face Erik Jones. Jones has shown vastly improved results on intermediates during their spring surge.

As well as Jones has performed, Hamlin has been the man to beat. For Denny to win his matchup he needs to continue his current run of form at the track type.

7. Buescher vs 10. Bell

Christopher Bell showcased his toughness after he completed a top ten run at Sonoma. He defeated Ross Chastain even with a broken wrist to advance to the second round.

His competition will be as stiff as his cast once more in the second round. Chris Buescher has ran the fifth most laps inside the top ten of all drivers this season and should continue with a strong run at another intermediate.

Bell looked as though he didn’t miss a beat last week. Combine his recovery with Toyota’s performances on intermediates gives him the edge to advance.

11. Byron vs 6. Larson

The second and final teammate battle of the round will see the Hendrick Motorsports duo of Kyle Larson and William Byron face off.

Larson enters Chicagoland with four straight top fives and looks primed to continue that streak at the intermediate track.

William Byron could face a real threat to his teammate as he finished higher than Larson at Las Vegas. But, Chicagoland should run very similar to Kansas Speedway and Larson will take full advantage of that and the tire test he completed at the track in late April.

14. van Gisbergen vs 3. Blaney

Someone had to matchup with Shane van Gisbergen at a road course and it was Ryan Preece. Now, van Gisbergen will face against another Ryan at Chicagoland.

Shane has shown great improvement in his intermediate performances in 2026.

While the growth is there, Ryan Blaney could be too tall of a task for Trackhouse Racing and van Gisbergen to handle.

Blaney is the lone winner in the Ford camp this season with his win at Phoenix. He also has an active six-race top ten streak which includes four races with the intermediate package.

If his hot streak can continue, Ryan Blaney should advance to the third round of the In-Season Challenge.