The Pensacola Pilots were a minor league level-B baseball team in the Southeastern League in 1927 and again from 1937-1942. The Pilots were a farmclub of the National League's Brooklyn Dodgers and Philadelphia Phillies. The Southeastern League consisted of teams such as the Meridian Millers, Montgomery Rebels, Jackson Senators, Vicksburg Billies, Selma Cloverleafs, Gadsden Pilots and Anniston Rams. From 1926-1930 the Southeastern League operated as a class-B loop. The circuit went out of operation for the 1931 season, reformed briefly in 1932, before collapsing on May 23rd of that year.
The Pilots played at their home games at Legion Field, a Pensacola ballpark fronting on Gregory and "H" Streets featuring a single-decked, wooden grandstand.
The team began as the Pilots and became a part of the league coached by Bill Holden. The Pilots would go 79-73 and finish fourth in the division.
In 1937, Pensacola re-joined the Southeastern League and were revived as the Pilots with Frank Kitchens named as manager. The team won the regular season campaign with an 83-52 record but lost in the finals.
In 1938, Wally Dashiell was selected manager and the team became a farm club of the Brooklyn Dodgers. The Pilots repeated with an even better record of 95-53 but were shocked in the first round of the playoffs.
The Pilots changed major league affiliations to the National League Philadelphia Phillies organization with Dashiell at the helm. The new parent team made no difference as the team went 87-48 and the squad took home the league championship for the first time ever.
In '40, the team went 89-60 with a narrow one game miss for the division. The Pilots would eventually lose in the league finals still a Phillies affliation.
In '41 Kitchens again became manager and the team slipped into fourth with a 75-67 record. Although a playoff berth, the squad exited early in the first round.
The '42 team was now managed by Buster Chatham, and later Jake Baker. Neither man could inspire the team as the Pilots endured their first losing season going 59-84 and a fifth place finish. The league closed up shop for the duration of World War II after the completion of the '42 season.
After the conclusion of World War II, the Southeastern League started anew in 1946. Pensacola's new team would be named the Fliers.