Monilaw got his first coaching job as the seventh head coach for his alma mater, the Drake University Dragons located in Des Moines, Iowa for two seasons, from 1903 until 1904. His coaching record at Drake was 10 wins, 7 losses, and 0 ties. This ranks him 11th at Drake in terms of total wins and fourth at Drake in terms of winning percentage.
From 1906 to 1908, he coached at the University of MissouriTigers in Columbia, Missouri where he compiled an 18-6-1 record. Monilaw was the 12th head coach for Mizzou and is ranked eighth at Missouri in total wins and sixth at Missouri in winning percentage.