Drivers who won their first NASCAR race in the Cup Series since 1990

Shane van Gisbergen’s victory in the inaugural Chicago Street Race was not only his first career Cup Series win — it also was his first start in any of NASCAR’s three national series.

It is rare to see a driver’s first NASCAR victory come in the Cup Series, with van Gisbergen’s victory being the 11th occurrence of it since 1990.

Take a look back at the 11 instances where a driver’s first NASCAR victory came in the Cup Series.

1990: Derrike Cope

Race leader Dale Earnhardt shredded a right-rear tire on the final lap of the 1990 Daytona 500, allowing Derrike Cope to take the checkered flag for the first time in his career. Cope, who had been driving in the Cup Series on and off since 1982, had yet to make an Xfinity Series start in his career at that point.

1990: Ernie Irvan

Ernie Irvan led the final 90 laps under the lights at Bristol in 1990 en route to his first Cup Series victory. It was just his 17th race behind the wheel of the No. 4 Kodak Film ride for Morgan-McClure Motorsports. The 31-year-old driver had made a handful of starts in the Xfinity Series, with a best finish of second coming three weeks earlier at Indianapolis Raceway Park.

1997: John Andretti

The wild conclusion to the 1997 Pepsi 400 at Daytona saw John Andretti finally capture his first career Cup Series victory. Andretti went on to make his Xfinity Series debut the following season and appeared in the Truck Series for the first time in 2005. 

1998: Jeremy Mayfield

Jeremy Mayfield entered the Cup Series race at Pocono in June 1998 with a 26-point lead in the standings over eventual series champion Jeff Gordon. He put an exclamation point on his lead by holding off Gordon to grab his first Cup Series victory that weekend. Mayfield had 20 career Xfinity Series starts at the time, with a best finish of seventh coming at Richmond in 1996.

1999: Tony Stewart

It seemed strange that Tony Stewart’s first Cup Series victory, which came at Richmond in 1999, was the first of his NASCAR career. At the time, Stewart had 37 total starts in the two other national series, capturing six top fives and eight top 10s over those starts.

2000: Jerry Nadeau

Jerry Nadeau seemingly came out of nowhere to capture a full-time Cup Series ride in 1998, with just 12 total NASCAR starts at the time. Fast forward to the 2000 Cup Series season finale, where he took the checkered flag in the No. 25 for Rick Hendrick. That victory came in the 111th start of his NASCAR career.

2001: Robby Gordon

Robby Gordon subbed for an injured Mike Skinner in the No. 31 Lowes Chevrolet in 2001, eventually leading to him taking over the ride full-time starting in 2002. Gordon went on to win the 2001 season finale, which was the first of his NASCAR career. 

2002: Jamie McMurray

Jamie McMurray took the No. 40 Coors Light Dodge to Victory Lane at Charlotte in 2002 for an injured Sterling Marlin in just the second start of his Cup Series career. That season was also the second full season of his Xfinity Series career, as he sat ninth in points at the time with no wins. It seemingly served as a breakthrough for the 26-year-old driver as he went on to win two of the next three Xfinity Series races.

2011: Trevor Bayne

Trevor Bayne shocked the world when he won the 2011 Daytona 500 in just his second career Cup Series start. He had 50 total Xfinity Series starts at the time, grabbing six top-fives and a pair of third-place finishes along the way.

2011: Regan Smith

Regan Smith’s victory in the 2011 Southern 500 at Darlington might go down as one of the biggest upsets in NASCAR history. The 27-year-old driver had made 104 Cup, 102 Xfinity and 23 Truck Series winless starts in his career and was driving for a team (Furniture Row Racing) that had never notched a top-five finish in 136 Cup Series starts.

2023: Shane van Gisbergen

Shane van Gisbergen conquered all the Cup Series regulars by winning the inaugural Chicago Street Race in 2023. It was the first NASCAR appearance for the 34-year-old and three-time Supercars champion.