The 2014 Orlando City SC season was the club's fourth season of existence in Orlando, and their final season before the team was elevated to Major League Soccer. The team entered the season as the defending USL Pro champions, beating Charlotte Eagles in the Championship Game after finishing second in the regular season.

On November 19, 2013, it was announced that Orlando City would be the next expansion franchise in Major League Soccer, the league's 21st team, to begin play in 2015. The announcement was made at Church Street Station in downtown Orlando, in the old Cheyenne Saloon, and was attended by an overflow crowd estimated by the Orlando Police Department at around 4,000. This made 2014 their final season in USL Pro.

Manager Adrian Heath said that the construction of the team for the 2014 season will be centered around getting players who can potentially move up with the team in 2015. As a result, he allowed several player contracts to lapse, only keeping a handful of vital personnel. He also signed goalkeeper Carl Woszczynski away from Los Angeles Blues, to play behind starting goalkeeper and team captain Miguel Gallardo.

Orlando City continued their affiliation with Sporting Kansas City through the MLS-USL Pro development alliance for the 2014 season. For the season, Sporting began transitioning their affiliation to Oklahoma City Energy FC, and would split their transfers between the two clubs before making Oklahoma City their sole affiliate in 2015.

The day before the MLS announcement, Orlando City and Orlando Health announced that the hospital system had signed a multi-year sponsorship contract which would make Orlando Health the team's presenting sponsor for its final USL Pro season, and going into MLS.

On June 3, 2014, Phil Rawlins sold Orlando City's USL Pro franchise license to minority owner Wayne Estopinal. While Orlando City moves on to MLS, the remaining USL Pro team will move to Louisville, Kentucky, in 2015 and become Louisville City FC. The team will maintain Orlando City's MLS colors. At the same time, James O'Connor retired as a player to become Louisville City's manager.

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