Dickenson attended Charles M. Russell High School in Great Falls, Montana, was an excellent student, and lettered in football, basketball, and golf. In football, he led his teams to two State Championships. Dickenson graduated from Charles M. Russell High School in 1991 with a 4.0 grade-point average. Dickenson's #15 jersey was soon retired by the school.
Dickenson is considered by many[who?] to be the greatest quarterback ever to play for the University of Montana. He owns numerous Big Sky Conference and Montana records. By the time he graduated in 1995, Dickenson had the highest completion percentage, highest percentage of passes for a touchdown, and fewest interceptions per pass in NCAA Division I-AA history. In his college career (including playoff games), he completed 1,015 of 1,477 passes (68.7%) for 13,486 yards with 116 touchdowns and only 26 interceptions, and was responsible for 137 total touchdowns (116 passing and 21 rushing).
In 1995, Dickenson's senior season, he threw for 5,676 yards in fifteen games, including 1,500 in four playoff games. Along with leading the Montana Grizzlies to a victory in the 1995 NCAA Division I-AA Football Championship Game, Dickenson won the 1995 Walter Payton Award as the outstanding offensive player in Division I-AA.

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