Bennett's first foray into managing was in 1923, with the
Cairo Egyptians of the
KITTY League. He replaced Jack Herbert and was one of two managers for the Egyptians that season. He would not manage again until 1928, with the
McCook Generals of the
Nebraska State League. He led them to league championships three years in a row, from 1928 to 1930, and a second-place finish in 1931. In 1928, the team seized first place after ten games, retaining that position for the rest of the year. They finished with a five-game lead over the second place
Lincoln Links. Due to his and the team's success that year, McCook led the league in attendance, and Bennett was named the All-Star team manager, along with three of his players. In 1929, the team finished 6.5 games over the second place
Fairbury Jeffersons. Although many teams were negatively affected by the
1929 Stock Market Crash in 1930, the Generals ended up having their best season, finishing 17 games over the Fairbury Jeffersons. They posted a record of 85–34. Over the course of his four-year tenure as manager of the Generals, he played in 77 of his team's games, or about 19 a year. In 1932, he led the
Waterloo Hawks of the
Mississippi Valley League to a losing record. He managed the Lincoln Links of the Nebraska State League for part of 1933 season before being replaced by Jack Hruska. After being fired by the Links, he served as a league umpire. He did not manage from 1934 to 1936. In 1937, he took over as manager of the
Norfolk Elks, a
New York Yankees affiliate in the Nebraska State League (which became the
Western League in 1939). Although he led the Elks to a losing record in 1937, he led them to a league championship in 1938 and a first-place finish in 1939, however the team lost in the first round of the playoffs that season. The Elks became the
Norfolk Yankees in 1940. Bennett led them to a first-place finish, though the team lost in the first round of the playoffs. From 1941 to 1942, Bennett managed the
Joplin Miners of the
Western Association, another Yankees affiliate. He led them to a first-place finish and a league championship in 1941, however they finished with a losing record and a fifth-place finish in 1942. Thus concluded his managerial career. ==Scouting career==