1975-77: Played as a backup quarterback for the University of Minnesota for three seasons.
1978: Transferred to Minnesota State for his senior season.
1978-79: Received invitations to training camp to play as a defensive back by the Minnesota Vikings.
1981-84: Begin his coaching career as a volunteer coach for the University of Miami. Trestman was promoted to quarterbacks coach in 1983, where he oversaw the development of Bernie Kosar.
1985-86: Returned to the Vikings as a running backs coach as part of the staff of Bud Grant, who was coming back from retirement.
1987: Served as the quarterbacks coach for the Tampa Bay Buccaneers during the strike-shortened 1987 season, which doubled as Vinny Testaverdes rookie year.
1988-89: Reunited with Bernie Kosar as the Cleveland Browns quarterbacks coach in 1988, and was promoted to offensive coordinator the next season.
1990-91: Returned to the Vikings for the final time to serve as a quarterbacks coach, where he worked with quarterback Rich Gannon for the first time.
1992-94: Out of coaching
1995-96: Got back into coaching as the offensive coordinator and quarterbacks coach of the San Francisco 49ers. With Steve Young at the helm, the 1995 49ers led the NFL in scoring and passing yards.
1997: Coached quarterbacks for the Detroit Lions. With Trestman, Scott Mitchell topped 3,000 yards passing for the final time in his career.
1998-2000: Filled the dual role of offensive coordinator and quarterbacks coach for the Arizona Cardinals. The 1998 Arizona Cardinals broke a 51-year franchise drought for playoff wins.
2001-03: Moved on to become the quarterbacks coach of the Oakland Raiders. When Trestman was promoted to offensive coordinator in 2002, the Raiders won the AFC and led the NFL in total offense and passing, and quarterback Rich Gannon won the MVP award.
2004: Served as the offensive coordinator of the Miami Dolphins and assistant head coach to Dave Wannstedt.
2005-06: Returned to college coaching to serve as the offensive coordinator for NC State.
2007: Out of coaching
2008-12: Traveled to Canada for his first head coaching job with the Montreal Alouettes of the CFL. In five years, Trestman has won two Grey Cups and lost in the final of a third.