Jeff Gordon By lienic Period: Jan 1, 1993 to Nov 22, 2015 Jeff Gordon Nov 24, 1993 Won Rookie of the Year Jan 1, 1994 Wins First Winten Cup Race Nov 1, 1995 Wins First Winston Cup Championshp Feb 1, 1997 Daytona 500 win Nov 1, 1997 Second Championship Nov 1, 1998 Third Championship Nov 1, 2001 Fourth Championship Feb 1, 2005 Won Daytona 500 Nov 22, 2015 Last Race in NASCAR Sprint Cup Series