While attending Duke, he played under coach Steve Spurrier and was named the 1988 ACC Football Player of the Year and the offensive MVP of the 1989 Hula Bowl. Dilweg holds the Duke single season record for passing yards with 3,824 in the 1988 season.
Dilweg was selected in the third round of the 1989 NFL Draft with the 74th overall pick by the Green Bay Packers. Dilweg is one of only 17 players to be selected in the NFL draft out of Duke. Dilweg's best NFL season was 1990 when he played 9 games with the Packers and threw for 1,267 yards and 8 touchdowns.
Today Dilweg is the Chairman of the Dilweg Companies, a real estate development company, and a sideline reporter for Duke. Dilweg and his wife, Jamie, have two daughters and one son.
Dilweg's grandfather, Lavern Dilweg, played end for the Packers from 1927-1934.