Dobie achieved his greatest success at the University of Washington, where he had a remarkable 58–0–3 record. During his tenure, Washington had a 40-game winning streak, which is the second longest in NCAA Division I-A/FBS history. His coaching career at Washington also comprised virtually all of Washington's 64-game unbeaten streak — still a college football record.
Dobie then became the 16th head coach for the United States Naval Academy Midshipmen and held that position for three seasons, from 1917 to 1919. His coaching record at the Navy was 18–3. This ranks him 14th at the Navy in total wins and first at Navy in winning percentage (.857), as of the end of the 2007 season.
After coaching at Navy, Dobie won three national championships with Cornell, in 1921, 1922, and 1923. During his first championship season at Cornell, he collected his 100th career win, doing so in 108 games—an NCAA record that stood until 2014, when Lance Leipold reached the mark in his 106th game at Division IIIWisconsin–Whitewater. Dobie remains the fastest coach to 100 wins in major-college history. His career coaching record was 182 wins, 45 losses, and 15 ties, a .780 percentage. Of the 33 years he coached, he had 14 undefeated seasons.