During the offseason, Orlando City parted ways with General Manager Niki Budalić who had been at the club since January 2016 and held the role of GM for two years.
[3] The club undertook its second major roster rebuild in as many years during James O'Connor's first winter transfer window in Orlando.
By the end of December the team had already sold Amro Tarek, Mohamed El Monir and Yoshimar Yotún who had all featured in major roles in 2018 while bringing in two of O'Connor's former Louisville City players Greg Ranjitsingh and Kyle Smith from USL,[4] as well as Ecuador international Sebas Méndez.
Luiz Muzzi continued to argue the case throughout the Combine and events leading up to the SuperDraft stating "We feel like the league did us wrong on this one."
[8] On February 18, Orlando unveiled Portuguese international winger Nani as a Designated Player, joining on a free transfer from Sporting CP.
[9] Orlando's fifth MLS campaign began at home to New York City FC on March 2, marking the third time the two 2015 expansion teams faced each other on opening weekend.
Designated player Nani scored his first goals for the club including an 89th-minute penalty to secure a 4–3 win over Colorado Rapids following a lengthy lightning delay at half-time.
[18] Orlando's final game in April was the reverse fixture of the season opener against NYCFC, ending in another draw like the first meeting.
Nani scored in his fourth consecutive game to equal Dom Dwyer's club record goal streak set in April 2018.
[26] On June 4, Orlando City held a press conference to announce the sale of the stadium's naming rights to Florida-based time share and vacation rental company Exploria Resorts.
[28] The following week, Orlando booked their place in the quarter-finals with a 2–1 victory after extra-time over fellow MLS side New England Revolution.
[33] Orlando would go on to draw the game 2–2, conceding a late equalizer to Kacper Przybyłko who had scored twice against the Lions earlier in the week.
[34] Following the game, an issue with the rescheduled travel arrangements meant the squad ended up stuck in Philadelphia for an additional second day.
"[37] When NYCFC won the coin toss and elected to kick the penalties in front of an empty South Stand, the opposite side of the stadium to The Wall where the Orlando City supporters were housed, the Orlando fans took it upon themselves to run en masse down the length of the concourse and fill up the stand directly behind the goal the penalties were being taken.
[38][39][40] Three days later, Orlando hosted Columbus Crew in the league, winning 1–0 courtesy of late Benji Michel goal, his first in MLS.
[41] However, the team ended July with a run of three games without a win, taking a point on the road in a 1–1 draw to Portland Timbers[42] before defeats to New York Red Bulls[43] and New England Revolution.
[45][46] On July 30, MLS debuted a new skills challenge event, pitting three teams composed of All-Stars (Wayne Rooney, Jonathan dos Santos and Carlos Vela), Atlético Madrid players (Koke, Héctor Herrera and João Félix) as well as players from Orlando City (Nani, Sebas Méndez and Chris Mueller) against each other in a series of games created by F2Freestylers.
[51] On August 10, the team earned a 1–1 draw against Toronto FC[52] before returning to Orlando for a midweek game against Sporting Kansas City, winning 1–0.
[54] However, two shutout losses to Atlanta United FC and San Jose Earthquakes to end August saw the team drop back down to ninth.
The result, coupled with New England's victory over NYCFC, officially eliminated the team from playoff contention with one regular season game left.
It broke the MLS record for most goals conceded in a single season set the previous year by Orlando City.
Orlando City entered the U.S. Open Cup in the fourth round, having been drawn against USL Championship team Memphis 901 FC.
In the Round of 16, Orlando beat fellow MLS team New England Revolution in extra-time to set up a quarter-final against New York City FC.