Ray Henningsen was born and raised in Omaha. He was an amateur and semi-pro star in Omaha which led him to a minor league contract with the Boston Red Sox organization. He started his career with Oneonta in the CanAm league in 1942 and finished the year with Greensboro in the Piedmont League. He batted .316 for Oneonta and .186 with Piedmont. He was in the Navy for the duration of the war then joined Omaha in 1947 as a member of the class "A" Omaha Cardinals in the Western League.
In 1947 he played every position except first base and pitcher. He spent most of his time at either second base, short or third. He eventually became a fixture at third base towards the end of the year. He was picked as most popular by the Omaha fans at the end of the season. The 1948 Cardinals program listed him as a Western League All Star but other sources do not.
He led the league in 1947 with 103 walks in 131 games. He also led the league with 16 sacrifice bunts.
In 1948 Ray moved to second base and led the Western League in fielding for the season. He was edged out by a Lincoln second baseman named Nellie Fox for the all star team. He played in 119 games for Omaha and Denver and averaged .307.