It was another wild NASCAR Cup race at Chicago with non-stop action from start to finish. Shane van Gisbergen sweeping the weekend was a rather predictable outcome, but it didn't take away from the fact that the race was full of epic storylines. In fact, there were so many winners and losers, we can't possibly mention them all here.
Some other 'winners' who didn't quite make the list: Kyle Busch, who came back from a lap down to score a top five, Austin Hill for scoring his first top ten in the Cup Series, Tyler Reddick for masterful charge at the end on fresh tires, and Denny Hamlin, who drove from last to fourth after an engine failure in practice.
Some other notable 'losers' would be the awkward misunderstanding that led to the clash between Joey Logano and Ross Chastain, William Byron's car breaking before the race even got underway, and Will Brown who came over from Supercars only for his NASCAR appearance to last less than three laps.
All of those moments and more were fit for this list, but each week, we try to stick to the five biggest winners and five biggest losers. So, here's a look at the ones we chose to really highlight...
WINNER: There's no stopping SVG on road and street courses
Van Gisbergen's abilities as a road racer are simply incredible, even surpassing fellow Supercars champion Marcos Ambrose, who once followed a similar path into NASCAR. He now has three Cup wins in just 33 career starts, is the winningest foreign-born driver in Cup Series history, and he swept the weekend in Chicago. He won from pole position in both the Cup and Xfinity races, and with another road course next weekend, he could potentially tie Denny Hamlin, Kyle Larson, and Christopher Bell for the most wins this year.
LOSER: Michael McDowell and what could have been
In Mexico City, Ty Gibbs was the only driver even close to SVG, and while he finished second in Chicago, Michael McDowell was the true threat. McDowell passed van Gisbergen at the start, led the most laps and won Stage 1. However, instead of snapping a two-year winless streak, he ended the day over 20 laps down when a throttle cable broke. But without that misfortune, he could have potentially spoiled SVG's weekend sweep and put the No. 71 Spire Motorsports Chevrolet into the playoffs.
WINNER: Ty Dillon gets one step closer to one million dollars
Since the start of NASCAR's in-season bracket challenge, I've had my eye on Ty Dillon. As the bottom seed, he should have been eliminated right out of the gate, but instead, he is one of the final eight drivers while 24 others have been eliminated. So far, he's defeated Denny Hamlin and now Brad Keselowski. Next up, he will face Alex Bowman and the might of Hendrick Motorsports. And what a story it would be if he were to go all the way and win the $1 million prize. And he's not the only underdog still in the fight. Both Legacy Motor Club drivers are still in it, but the teammates will face each other at Sonoma, ensuring one is elimianted.
LOSER: Carson Hocevar makes a costly mistake
Just two laps into the Chicago Street Course race, Hocevar made an unforced error that ended both his day the days of several others. It's been a rocky month for him, getting into it with Ricky Stenhouse Jr., facing internal penalties from his own team after making offensive comments about Mexico, all while he keeps slipping deeper into the standings. In Chicago, he hit the wall and spun in front of the field, collecting many other drivers. An error like that surely won't make him anymore friends, and he already has plenty of enemies on track.
WINNER: Katherine Legge defies the doubters, scoring a career-best finish
Legge's journey in NASCAR has been a difficult one, marred by mistakes and crashes. And while she faced plenty of adversity in Chicago, she overcame it all for her best showing yet. First, Legge made the race over 23XI Racing and Corey Heim in an unlikely upset. And during the race, she earned a top 20 finish (19th) in the No. 78 Live Fast Motorsports Chevrolet. Not only was it her best finish yet in a NASCAR Cup car, but it matched the team's best result ever at a non-drafting track.
LOSER: Bubba Wallace's good day goes bad after run-in with Alex Bowman
Wallace rallied back from a mid-race spin to run inside the top ten in Chicago. However, when his old rival in the No. 48 caught him, things unraveled quickly. Not only were they battling for position on track, but also for a spot in the next round of the in-season challenge. There was a lot of contact that ended with Wallace spinning out, losing 20 spots in the process. The incident now puts him right on the cut-line in the playoffs, just three points above Ryan Preece.
WINNER: The weather in Chicago played nice (for once)
For the first two years of the Chicago Street Course event, rain impacted the Cup race. However, while there was weather in the area, it stayed away until after the checkered flag, allowing for a fully dry race for the very first time. And as we all saw, we didn't need rain to make things exciting, as there was still plenty of action all around the track. It also brought tire wear into the picture with fresh rubber having quite the impact on the race.
LOSER: NASCAR's questionable officiating
Oh my goodness, the impact for Cody Ware into the tire barrier with two laps to go is even harder and more intense than I could have imagined. Thankfully, he was able to walk away. Man... #NASCAR pic.twitter.com/B8lPGNWOjW
— Toby Christie (@Toby_Christie) July 7, 2025
Unfortunately, NASCAR officiating is once again in the spotlight. There were some moments where they waited far too long to throw the caution flag, but none as egregious as the very end of the race. Cody Ware suffered a brake failure that sent him head-on into the wall at Turn 6. It was the biggest hit of the race and he radioed his team that he might need help. However, NASCAR still waited, and by the time they saw it fit to throw the yellow, SVG had already taken the white flag -- the race was over. While some fans were annoyed about being robbed of an overtime restart, the real issue was one of safety. Ware sat in the car for over 30 seconds before the caution was displayed, which is way too long for the severity of the crash. Thankfully, he was later checked and released from the infield care center.
