In 1991, he gained new sponsorship from Pennzoil and won the Winston Open, as well as his first two career pole positions. He came close to winning the 1991 Transouth 500 with the team but had an incident that put him out of the running. Waltrip would have to wait 10 more years to get his first win. He stayed with the Bahari team until the end of 1995, when he was replaced by rookie Johnny Benson. He joined Wood Brothers Racing to drive their #21 Citgo Ford. He won the 1996 edition of The Winston . After posting one top-five finish over a period of three years, and missing his first race since 1986 at the 1998 Dura Lube/Kmart 500, Waltrip departed the Woods at the end of 1998 to drive the #7 Philips Chevrolet for Mattei Motorsports, posting three top-ten finishes and ending that season 29th in points. The next season, Nations Rent replaced Philips as the sponsor & he moved up to twenty seventh in points but finished in the top-five once, causing him and the team to part ways at the end of the season.
Waltrip was hired by Dale Earnhardt, Inc. to drive their new #15 NAPA Chevy entry. In his first race with the team, the 2001 Daytona 500, Waltrip broke a streak of 463 consecutive Cup races without a victory and won his first career points-paying Cup race. After the death of his boss Dale Earnhardt, he did not have another top-ten finish until the Pepsi 400, and finished 24th in the standings. The next season, he picked up his second career win at the Pepsi 400 and moved up to fourteenth in the standings. Throughout 2003, he won a career-high two races including his second career Daytona 500 win, and ran in the top-five for most of the season before falling back to 15th in points. Of trivial note, Michael Waltrip won the first three races at Daytona on Fox (2001, 2003 Daytona 500; 2002 Pepsi 400) with Waltrip's brother Darrell in the broadcast booth.
No speeding in the Park. Bicycles are allowed on all two tracked trails. Do not bike on single tracked trails. Wheels yield to feet, (Hikers and horses). Hikers yield to horses.
Cache placement approved by Martin Morse, Park Service Specialist. Obey all speed limits. Do not block gates. All wheels off the pavement.