Some drivers take the long road through Xfinity and Trucks before winning in the Cup, but these racers defied expectations. Whether by skill, opportunity, or sheer luck, they secured Cup Series victories before ever stepping into NASCAR’s lower tiers. Their wins weren’t just career milestones—they were moments that shook up the sport’s history.

5. Tony Stewart

Can You Believe? 11 Drivers Who Won in the Cup Series Ever Before Xfinity and Trucks Ft Tony Stewart

Derrike Cope wasn’t expected to win the 1990 Daytona 500, but when Dale Earnhardt blew a tire on the final lap, Cope capitalized. He crossed the finish line first, scoring his first NASCAR victory in dramatic fashion. At the time, Cope had never made a start in the Xfinity Series, making this underdog win even more remarkable.

6. Derrike Cope (1984)

1. 1990: Derrike Cope

2. 1990: Ernie Irvan

John Andretti found Victory Lane for the first time in the 1997 Pepsi 400 at Daytona. His breakthrough Cup win came before he had ever raced in the Xfinity Series. He later competed in both Xfinity and Trucks, but his Cup win remains one of the biggest moments of his NASCAR career.

3. 1997: John Andretti

Jeremy Mayfield’s first Cup win came at Pocono in 1998 when he held off Jeff Gordon to take the checkered flag. Though he had made 20 Xfinity starts by then, his best finish was only seventh. This Pocono victory cemented Mayfield as a serious contender in the Cup Series.

4. 1998: Jeremy Mayfield

Tony Stewart’s first Cup win at Richmond in 1999 was just the beginning of a Hall of Fame career. Though he had 37 starts across Xfinity and Trucks, he had never won in either series before claiming his first Cup victory. Stewart would go on to become a three-time Cup champion.

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5. 1999: Tony Stewart

Jerry Nadeau’s journey to his first Cup win was unconventional. With only 12 total NASCAR starts before securing a full-time Cup ride in 1998, Nadeau finally broke through at the 2000 season finale in the No. 25 car for Rick Hendrick. It was his only career Cup win, but one that fans still remember.

6. 2000: Jerry Nadeau

Robby Gordon stepped in for an injured Mike Skinner in 2001 and made the most of his opportunity. Driving the No. 31 Lowe’s Chevrolet, he won the season finale, earning his first NASCAR victory before competing in Xfinity or Trucks. His road racing background made him a unique talent in the Cup Series.

7. 2001: Robby Gordon – Stepping Up in a Substitute Role

Jamie McMurray shocked the NASCAR world when he won at Charlotte in just his second Cup Series start. Filling in for an injured Sterling Marlin, McMurray pulled off a historic victory. At the time, he was in his second full season in Xfinity but had not yet won there. His breakthrough in Cup set the stage for a successful career.

10. Jamie McMurray (2002)

8. 2002: Jamie McMurray

Trevor Bayne stunned everyone by winning the 2011 Daytona 500 in just his second Cup Series start. Though he had 50 Xfinity races under his belt, he had never won in that series before his triumph at Daytona. At just 20 years old, Bayne became the youngest Daytona 500 winner in history.

1. Trevor Bayne’s Stunning Win (2011)

9. 2011: Trevor Bayne

Regan Smith pulled off one of NASCAR’s biggest upsets, winning the 2011 Southern 500 at Darlington. Before that victory, Smith had gone winless in 104 Cup, 102 Xfinity, and 23 Truck Series starts. His triumph for Furniture Row Racing, a team without a previous top-five finish, was a milestone moment.

Regan Smith – The “Underdog Story” That Didn’t Last (2011)

10. 2011: Regan Smith

Shane van Gisbergen made history in 2023 by winning the inaugural Chicago Street Race in his first-ever NASCAR appearance. The three-time Supercars champion took on the Cup Series regulars and outdrove them all. Without any prior experience in Xfinity or Trucks, he became just the latest driver to win in the Cup before competing in NASCAR’s lower divisions.