In 1991 Wallace took the Miller sponsorship with him to Penske Racing,[4] and he continued in the #2 Miller Genuine Draft Pontiac. He also won the 1991 IROC championship.

While 1992 only carried him one win, the win at the Miller 400 was satisfying; it was the first win for Rusty in a car which arguably was Rusty's best known chassis for his career, one affectionately known as "Midnight" after the win. "Midnight" would be raced for six seasons, carrying various race wins, before being retired in 1997.

1993 was arguably his most successful season despite two major accidents at Daytona and Talladega in which his car went airborne and flipped several times. He had already won the second race of the season Feb 28th 1993 at North Carolina Motor Speedway but also a sad one as his friend and reigning NASCAR Champion Alan Kulwicki was killed flying into Bristol Speedway in April 1993, because of this Rusty won the race at Bristol and in respect to Alan Kulwicki he did a "Polish victory lap"—turning his car around and driving around the track the wrong way, as made famous by Kulwicki. Every race Rusty won that year he did a "Kulwicki victory lap". He won all 3 races in April (Bristol 4/4/93, North Wilkesboro 4/18/93 and Martinsville 4/25/93). Also he won the first ever race at the New Hampshire Speedway starting 33rd on July 11. In 1993, he won 10 of the 30 races,[5] but finished second in the final points standings, 80 points behind Earnhardt. He ended the season strong, finishing in the Top-3 in all but two of the final ten races of the season.

Penske switched to Fords in 1994.[5]

In 1996, sponsorship changed from Miller Genuine Draft to Miller beer sponsorship.

1997 paint scheme

In 1997, Miller changed the teams sponsorship to Miller Lite, replacing the black and gold with a blue and white scheme.

In 1998, Wallace won the Bud Shootout at Daytona, A non-points race for the previous years pole winners and past winners of the race. It was the first win for Ford's new Taurus, and Wallace's only victory at NASCAR's premier track (as well as his only victory in any restrictor plate race) in a Cup car

In 2003, Penske Racing switched to Dodge, and appropriately, in 2004, Wallace won his 55th, and final, race on a short track: the 2004 spring Martinsville Speedway race. It was also the last win for the track under the ownership of the H. Clay Earles Trust; the death of Mary Weatherford (matriarch of the trust) forced the Trust to sell the track a month later.

On August 30, 2004 Wallace announced that the 2005 NASCAR NEXTEL Cup season would be his last as a full-time driver. Although at the time the possibility remained that he may have continued to run a limited schedule after the 2005 season—as semi-retirees Bill Elliott and Terry Labonte also have done, Wallace's current broadcasting contract forbids him from doing so. Kurt Busch would replace Wallace in the number 2 Miller Lite Dodge in 2006-2010. In 2011, Brad Keselowski will drive the number 2.

In 2006, Wallace returned to his General Motors roots when he raced a Crawford-Pontiac sportscar, painted black and carrying the familiar stylised #2. The car was sponsored by Callaway Golf, in the Rolex 24 at Daytona, teamed with Danica Patrick and Allan McNish; in 2008, his NASCAR Nationwide Series cars switched from Dodge to Chevrolet.

To date, Rusty had 55 NASCAR Cup wins, which is tied for 8th on NASCAR's all-time wins list. They include victories at Charlotte as well as the series' last three road courses (Riverside, Infineon and Watkins Glen), but none at Daytona, Darlington, Indianapolis or Talladega. Wallace has the most short track wins in NASCAR history with 34, and therefore he is considered among the best short track drivers in NASCAR history. He retired after the 2005 season with a 14.4 career average finish.