He worked in the playoffs 18 times, including every season from 1998 through 2006. He appeared in five World Series (1988, 1992, 1998, 2000, and 2002), serving as crew chief in 1992 and 2002; twelve League Championship Series (1980, 1983, 1985, 1990, 1993, 1995, 1996, 1999, 2001, 2003, 2005, and 2006), with all but the last two being in the NL; and five Division Series (1981, 2000, 2002, 2004, and 2010). His 11th appearance in the League Championship Series in 2005 broke the record he had previously shared with Bruce Froemming. He also umpired in the All-Star Game in 1989 and was the home plate umpire for the 2006 All-Star Game. On May 23, 2002, Crawford was the second base umpire for Shawn Green's four-homer game. He was at third when Carlos Delgado hit four homers on September 25, 2003. As his father worked the first game at Philadelphia's Veterans Stadium on April 10, at home plate, Crawford worked home plate in the last game at "The Vet" on September 28, and repeated the honors when Citizens Bank Park opened April 12, .