After being an also-ran for their first two seasons of field competition, The Cavaliers won their first contest in 1952. At the Spectacle of Music in South Milwaukee, The Cavaliers were winners in Class B (while all the corps they considered to be "Big Corps" were in Class A). They went on to win the Iowa State Fair contest and capped the season by finishing in seventh place at their first American Legion Junior National Championship in New York City, and won the General Effect caption. Although the corps was becoming a midwest powerhouse, The Cavaliers were far behind the top corps in drumming. In 1955, the staff added Frank Arsenault, considered to be the best rudimental drummer of his day, to work with the drummers. In 1956, the Cavaliers had risen to the number one ranking in the midwest, but could only manage a third-place finish at VFW Nationals. However, in 1957, after trading victories with the Madison Scouts and the Belleville Black Knights, The Cavaliers won not only both the Illinois State American Legion and VFW titles, but also their first VFW National title in Miami. Their win broke the stranglehold that the East Coast corps had held on the national championships. Although the win was considered by the East Coast corps to be just a fluke, the Cavaliers repeated as VFW champions two years later in Los Angeles.