Fleming Stadium, originally known as Wilson Municipal Stadium, was built in 1938 as a WPA project. The stadium was officially dedicated on June 29, 1939. The Wilson Tobs were playing this first season in the stadium. In 1952 the stadium was renamed Fleming Stadium in memory of Allie W. Fleming, a local businessman who also happened to be President of the Wilson Baseball Club in 1939.

Professional teams playing in Wilson's Fleming Stadium have been the Coastal Plain League Class D 1939-1941, Bi-State League Class D 1942, the Coastal Plain League Class D 1946-1956, the Carolina League Class B 1956-1968, and the Carolina League Class A 1973.

Boston Red Sox Hall of Famer Ted Williams played in Fleming Stadium in an exhibition game against the Philadelphia Phillies. Some legendary baseball figures who played minor league ball in Fleming Stadium include Rod Carew, Curt Flood, Cal Ripken, Sr., Willie McCovey, Carl Yastrzemski, Bobby Murcer, Rusty Staub, Leon Wagner, Jimmy Hall, Richie Hebner, Micky Lolich, Tony Taylor, Donn Clendenon, Fred Valentine, Bob Veale, Caesar Tovar, Al Oliver, Tony Perez, Rico Petrocelli, Mel Stottlemyre, Chuck Witherspoon, and Dick McAuliffe.

In fact, the 1941 Wilson Tobs team was voted number 82 of the top 100 teams in the history of minor league baseball. This team had a sparkling 87-30 record (a .744 winning percentage), led the league in six different categories, had two 20+ game winning pitchers, and were managed by a 28 year old pitcher who had a 16-3 record with 19 complete games and three shutouts.

The largest crowd to see a baseball game at Fleming Stadium was during the 1940 season when the Wilson Tobs played the Greenville Greenies. It was estimated that 10,000 fans attended the game which included a public address by Mayor Fiorello LaGuardia of New York City, the Big Apple's "Little Flower". The largest Fleming Stadium fan attendance year was in 1946 when the playoffs pushed attendance to almost 180,000.

The Stadium originally had 3,000 seats in the grandstand. After many years of deterioration, the City began renovation on the Stadium in 1994 that continued through 1998. All the original seats were removed and new seats, with handicapped seating, were installed. The City continues to make improvements as needed in providing a quality playing field and at the same time to keep the "ball park integrity" of a venerable baseball stadium. However, to meet the new standards and construction of a Press Box the number of grandstand seats were reduced to 2,525.

Since 1997, the Coastal Plain League Summer Collegiate Baseball Wilson Tobs has played their home games in venerable Fleming Stadium. Fleming Stadium is the flagship of this exciting summer league which has grown to thirteen teams in 2003, operating in NC, SC and VA.