As of the 2008 season, that has occurred twice. In Super Bowl VII, the Miami Dolphins were undefeated and played the Washington Redskins. The Dolphins won, 14-7, to complete their undefeated season (17-0). In Super Bowl XLII, the New England Patriots were undefeated and played the New York Giants. The Patriots lost, 17-14, and finished the season at 18-1.
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Yes. Several times. Here's a list of winless teams in pro football. I included some teams who didnt lose every game, but none the less, didn't register a single victory. NFL Franchises
Chicago Cardinals (Arizona Cardinals)
1943 0-10 Dallas Cowboys
1960 0-11-1 Detroit Lions
1942 0-11 Indianapolis Colts (Baltimore Colts)
1982 0-8-1 in a strike shortened season Tampa Bay Bucanneers
1976 0-14
Historical NFL/APFA Franchises - noted that these teams did not all play a tandardized schedule. The number of games varied year to year, and club by club. Brookyln Tigers fka Brooklyn Dodgers & the Dayton Triangles
1944 0-10
1929 0-6
1928 0-6
1925 0-7-1 Buffalo All Americans f/k/a Buffalo Rangers & Bisons
1927 0-5 Chicago-Pittsburgh Carpets (a combined Pittsburgh Steelers & Chicago Cardinals roster)
1944 0-10 Cincinnatti Reds
1934 0-8 Colombus Tigers f/k/a Colombus Panhandles
1925 0-9
1022 0-8
1920 0-5 Newark Tornadoes f/k/a Orange Tornadoes, Duluth Eskimos & Duluth Kellys
1925 0-3 Evansville Crimson Giants
1922 0-3 Hammond Pros
1926 0-4
1922 0-5-1
1920 0-3 Kenosha Maroons f/k/a Toledo Maroons
1924 0-4-1 Louisville Brecks
1923 0-3
1921 0-2 Louisville Colonels
1926 0-4 Milwakee Badgers
1925 0-6 Minneapolis Marines
1924 0-6 Muncie Flyers
1921 0-2
1920 0-1 New York Brickley's Giants
1921 0-2 Rochester Jeffersons
1925 0-6-1
1924 0-7
1923 0-4
1922 0-4-1
1920 0-1 Tonawanda Kardex
1921 0-1
The Miami Dolphins and and the New England Patrots have gone undeafted in a regular season.
The 1972 Miami Dolphins entered the Super Bowl 16-0 and won. The 2007 New England Patriots entered the Super Bowl 18-0, but lost.