In a straight shootout with his JR Motorsports teammate Connor Zilisch, the Kiwi stole the lead on the second-to-last lap.
Driving the #88 Chevrolet Camaro, Zilisch led the field to green. The race-defining moment came when van Gisbergen got the nose of his #9 Camaro up the inside into Turn 1.
Van Gisbergen forced Zilisch wide and he brushed the wall out of Turn 1. Van Gisbergen left Zilisch to fend off Sheldon Creed and Austin Hill, managing to maintain second through Turn 2.
The young gun tried to fight back, but van Gisbergen held sway to clinch the win by a few car lengths.
Van Gisbergen had to strategise his way to victory, opting to win Stage 1 while the lion’s share of the field behind him pitted.
The #9 team elected to pit later in the race. That gave him slightly fresher tyres and more fuel, but meant he was buried in the field and had to charge his way through from outside the top 20.
“Unreal. I thought it was going to be a lost cause when the strategy went wrong. It worked out well,” said van Gisbergen.
“I knew that was what we were going to do, but when so many cars didn’t follow us, it was a bit of a worry. Then we had tyre grip at the end. Really cool battles there with everyone. I enjoyed it.”
Before Chicago, Zilisch had beaten van Gisbergen in the head-to-head stakes in their four previous NASCAR Xfinity Series contests.
The 18-year-old was left to lament the race restart.
“I guess I should have just not let him get to my bottom,” said Zilisch.
“I was clear there. Just barely on the front straight and just let him get to my inside and took advantage of it.
“Hate it for my #88 group. I should have just been a little more aggressive there. I just thought he was going to race me a little cleaner. I’ll learn from it, move on.
“Really cool to have Red Bull, WeatherTech schemes one-two. Our car was as fast as Xfinity Mobile all day, even after the damage. Looking forward to getting back after it.”
Asked if the contact was “not fair”, Zilisch said it was fair game.
“It’s racing for the win. I’m not going to complain about it. He won the race and I didn’t,” he said.
“I’ve just got to be better and not let that stuff happen
“I’ll learn from it, move on, and look forward to racing him again next week at Sonoma.”
It marked his second straight Xfinity Series win after triumphing a year ago with Kaulig Racing in the #88 Chevrolet Camaro.
On the restart, van Gisbergen said he had to make the most of the chance.
“He’s a great young driver. It’s the first time I’ve really raced him and I knew that was my opportunity and took it. It was an awesome one-two for the team,” said van Gisbergen.
Van Gisbergen will swap the #9 JR Motorsports Camaro for the #88 Trackhouse Racing Camaro on Monday (AEST) and have a chance to sweep the weekend from pole position.
“I would love to,” he said.
“I’m lucky. I’ve got some great cars this weekend driving for some great teams. I really look forward to tomorrow.”
Jack Perkins was the victim of an early crash. He appeared to suffer a hit from JR Motorsports’ Sammy Smith during Stage 1, which tipped the #19 Joe Gibbs Racing Toyota Supra into a spin and into the wall.
Results: NASCAR Xfinity Series The Loop 110, Chicago Street Course
| Pos | Num | Driver | Team | Laps/Diff | Gap |
| 1 | 9 | Shane Van Gisbergen | JR Motorsports | 50 laps | |
| 2 | 88 | Connor Zilisch | JR Motorsports | 0.823 | 0.823 |
| 3 | 0 | Sheldon Creed | Haas Factory Team | 3.141 | 2.318 |
| 4 | 21 | Austin Hill | Richard Childress Racing | 4.186 | 1.045 |
| 5 | 48 | Nick Sanchez | Big Machine Racing | 5.876 | 1.690 |
| 6 | 2 | Jesse Love | Richard Childress Racing | 6.786 | 0.910 |
| 7 | 8 | Sammy Smith | JR Motorsports | 7.792 | 1.006 |
| 8 | 41 | Sam Mayer | Haas Factory Team | 8.921 | 1.129 |
| 9 | 32 | Austin Green | Jordan Anderson Racing | 8.955 | 0.034 |
| 10 | 44 | Brennan Poole | Alpha Prime Racing | 9.153 | 0.198 |
| 11 | 11 | Josh Williams | Kaulig Racing | 9.409 | 0.256 |
| 12 | 7 | Alex Labbe | SS-Green Light Racing | 9.693 | 0.284 |
| 13 | 25 | Harrison Burton | AM Racing | 10.938 | 1.245 |
| 14 | 26 | Dean Thompson | Sam Hunt Racing | 12.18 | 1.242 |
| 15 | 16 | Christian Eckes | Kaulig Racing | 12.512 | 0.332 |
| 16 | 1 | Carson Kvapil | Kaulig Racing | 12.592 | 0.080 |
| 17 | 70 | Thomas Annunziata | Cope Family Racing | 13.602 | 1.010 |
| 18 | 31 | Blaine Perkins | Jordan Anderson Racing | 14.233 | 0.631 |
| 19 | 10 | Daniel Dye | Kaulig Racing | 14.777 | 0.544 |
| 20 | 28 | Kyle Sieg | RSS Racing | 16.192 | 1.415 |
| 21 | 20 | Brandon Jones | Joe Gibbs Racing | 16.502 | 0.310 |
| 22 | 24 | Kaz Grala | Sam Hunt Racing | 16.619 | 0.117 |
| 23 | 7 | Justin Allgaier | JR Motorsports | 16.758 | 0.139 |
| 24 | 4 | Parker Retzlaff | Alpha Prime Racing | 17.664 | 0.906 |
| 25 | 71 | Ryan Ellis | DGM Racing with Jesse Iwuji Motorsports | 18.516 | 0.852 |
| 26 | 14 | Connor Mosack | SS-Green Light Racing with BRK Racing | 22.259 | 3.743 |
| 27 | 27 | Jeb Burton | Jordan Anderson Racing | 22.577 | 0.318 |
| 28 | 99 | Matt DiBenedetto | Viking Motorsports | 22.618 | 0.041 |
| 29 | 50 | Preston Pardus | Pardus Racing Inc. | 28.539 | 5.921 |
| 30 | 45 | Brad Perez | Alpha Prime Racing | 45.885 | 17.346 |
| 31 | 51 | Jeremy Clements | Jeremy Clements Racing | 48.218 | 2.333 |
| 32 | 19 | Jack Perkins | Joe Gibbs Racing | 4 laps | |
| 33 | 35 | Andre Castro | Joey Gase Motorsports with Scott Osteen | 7 laps | 3 laps |
| 34 | 54 | Taylor Gray | Joe Gibbs Racing | 12 laps | 5 laps |
| 35 | 91 | Josh Bilicki | DGM Racing with Jesse Iwuji Motorsports | 24 laps | 12 laps |
| 36 | 42 | Anthony Alfredo | Young’s Motorsports | 24 laps | |
| 37 | 18 | William Sawalich | Joe Gibbs Racing | 43 laps | 19 laps |
| 38 | 39 | Ryan Sieg | RSS Racing | 45 laps | 2 laps |
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