Dale Earnhardt Jr. won his first Nascar Cup Series race on April 2, 2000 at Texas Motor Speedway. He also won his first Nationwide race, then known as the Busch Series, at Texas Motor Speedway on April 4, 1998.
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By the Cup do you mean the Championship, he has never won the Sprint Cup, Nextel Cup, or the Winston Cup Championship, he has however won the Busch Series Championship twice in 1998 and 1999.
If your referring to individual wins in the Winston "Cup", here's that info:
Became first driver since Bill Elliott at Michigan 1985-6 to win four straight races on one superspeedway, doing so at Talladega October 2001 through April 2003.
Entering July 2003, had won the following races in Winston Cup - 2000 Texas 500 and Richmond 400, 2001 Firecracker 400, Delaware 400, and EA Sports 500, 2002 Alabama and EA Sports 500s at Talladega, 2003 Alabama 500.
Dale Sr. won his first Nascar Winston Cup race on April 1, 1979 at Bristol International Speedway.
He won his first Busch Series race on February 13, 1982at Daytona International Speedway.
Dale Jr's last Nascar Cup Series win was the GoBowling.com 400 on August 3, 2014 at Pocono Raceway.
His last Nascar Nationwide Series win was on July 2, 2010 at Daytona International Speedway.
Dale Sr. won his first Nascar Winston Cup race on April 1, 1979 at Bristol International Speedway. He won his first Busch Series race on February 13, 1982 at Daytona International Speedway.
Dale Sr's first Nascar Cup Series race was on May 25, 1975. It was the World 600 at Charlotte Motor Speedway. He started 33rd and finished 22nd.