Pre-season 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. He was replaced in the role by
FC Dallas vice president of soccer operations Luiz Muzzi. The day after Budalić departed, the club announced that a total of nine players were out of contract, most notably captain
Jonathon Spector marking the second consecutive season the team's captain had left following
Kaká's retirement a year earlier. 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, as well as
Ecuador international
Sebas Méndez.
Benji Michel was signed to a
Homegrown deal, becoming the club's fifth homegrown player; the first to be born in Orlando and come up through the Development Academy. The team also tried to sign
Santiago Patiño to a Homegrown contract but the move was controversially blocked by
MLS. 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." Orlando eventually decided to draft him with their #3 overall pick with O'Connor describing the selection as "a message to all our other homegrowns." Orlando announced six preseason matches for 2019 including the inaugural iteration of the OC Invitational, a preseason friendly tournament that would feature
New York City FC,
New England Revolution and
Minnesota United FC with each team facing two of the other three participants. It marked only the second time that the club would play preseason games open to the public following a friendly against
Bahia in February
2016. The Lions lifted the OC Invitational trophy after winning both of their games against
New York City FC and
New England Revolution.
Minnesota United FC would finish on the same record but with worse goal difference. On February 18, Orlando unveiled
Portuguese international winger
Nani as a
Designated Player, joining on a free transfer from
Sporting CP. The following week Orlando traveled to
Chicago for their first road game of the season. The game ended 1–1 when
C.J. Sapong equalized for 10-man
Fire in the final minute. It marked the first time since April 29, 2018 that Orlando had earned any points away from home. The first defeat of the season came in week three as Orlando lost 3–1 to
Montreal Impact at home.
Ignacio Piatti scored a brace to take his all-time individual total against the Lions to 10 goals in 10 games, the most of any single player against Orlando in MLS while Orlando City goalkeeper
Brian Rowe was forced into a career-high eight saves. The following week, Orlando went to reigning
Supporters' Shield winners
New York Red Bulls and got their first win of the season. Former Red Bulls captain
Sacha Kljestan scored the only goal of the game as the Lions got their first road win since April 29, 2018, the first of James O'Connor's reign, and also kept their first clean sheet on the road since April 13, 2018. The month ended with a 2–1 defeat to
D.C. United. The result followed a series of controversial calls on the
Rooney goal including a phantom foul, incorrect ball placement and impeding of the Orlando goalkeeper, none of which were called or looked at by
VAR and led to a post-match tirade by O'Connor who slammed the officiating.
April On April 6, Orlando earned their first home win of the season. 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. Orlando's first away loss of the season was on April 13 when they fell 2–1 to
Real Salt Lake. It was the first time in the teams' five meetings that RSL had won. In their next game, Orlando earned their first ever victory over
Vancouver Whitecaps FC with
Nani deflecting in a late 88th-minute winner. 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.
May On May 2,
MLS officially announced
Atlético Madrid as the opposition for the
2019 MLS All-Star Game set to be hosted by
Orlando City SC at
Orlando City Stadium on July 31. On May 4, the team were held scoreless for the first time on the year in a 2–0 home defeat to
Toronto FC. They had their second consecutive shutout loss a week later against Atlanta. On May 19, Orlando played new expansion side
FC Cincinnati for the first time, beating them 5–1. It was the first time since May 6, 2018 that Orlando had won a game by more than one goal. The team ended with a frustrating 1–0 defeat to
LA Galaxy having out-shot the visitors 19–4. On May 29, the team announced plans to move all of Orlando City's development pyramid to one single site, creating a new 20-acre state-of-the-art training complex at Osceola Heritage Park to house the senior team as well as OCB and the Development Academy.
June On June 1, Orlando opened the month with a 3–0 victory away to
Montreal Impact, the team's first road win by multiple goals since April 13, 2018 when the Lions earned a 2–0 win over
Philadelphia Union. 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. As a result, the stadium was renamed
Exploria Stadium. On June 12, the team won their opening
U.S. Open Cup game of the year 3–1 over
USL Championship side
Memphis 901, to progress to the Round of 16. The game was notable for
Robin Jansson's first goal as a Lion. 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. On June 26, Orlando played their first league game since June 1 following two Open Cup matches. They lost 1–0 to
D.C. United after
Wayne Rooney scored from within his own half. The team's final game of June was away to
Columbus Crew, a 2–0 victory to give the team their first winning record in June since their inaugural season in MLS.
July July opened with back to back games against
Philadelphia Union home and away. On July 3, Orlando lost 3–1 at home with
Jansson and
Kljestan both receiving red cards during the game. The away match was originally scheduled for July 6 but a pre-match adverse weather delay due to lightning storms turned into a full postponement with MLS rescheduling the game for the next day - a decision that was not received well by Orlando City as it not only impacted the team's U.S. Open Cup quarter-final preparations but there were also three major international tournament finals on that day:
Women's World Cup,
Copa América and
Gold Cup. 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. Following the game, an issue with the rescheduled travel arrangements meant the squad ended up stuck in Philadelphia for an additional second day. On July 10, Orlando City progressed to their first ever U.S. Open Cup semi-final, beating
New York City FC on penalties after a 1–1 draw with
Maxi Moralez scoring a 90+6-minute equalizer to send the game into
extra-time.
Adam Grinwis made two saves in the
shoot-out. The game received viral media coverage for what became known as
"The Running of The Wall." 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. Three days later, Orlando hosted
Columbus Crew in the league, winning 1–0 courtesy of late
Benji Michel goal, his first in MLS. 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 before defeats to
New York Red Bulls and
New England Revolution. Orlando hosted
2019 MLS All-Star week at the end of July. On July 29, Orlando City's
eMLS professional
FIFA player FIFA Abe, alongside guest player AnthFifa, won the eMLS All-Star Challenge that also featured
Landon Donovan and
Diego Forlán. The victory earned $5,000 for the Orlando City foundation. 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. The event, held at the
ESPN Wide World of Sports Complex, was won by the Orlando City team after Nani hit the crossbar with the last kick of the competition, winning an additional $25,000 for the Orlando City Foundation. Nani was Orlando City's sole representative in the All-Star Game, coached by
James O'Connor and won 3–0 by Atlético, while
Benji Michel and
Mason Stajduhar both featured in the
2019 MLS Homegrown Game.
August Orlando went on their longest unbeaten run in the league during August, avoiding defeat in four games. On August 3, Orlando returned to MLS action to record the team's first ever win over
FC Dallas. Former Dallas player
Tesho Akindele opened the scoring in his first appearance against the team following a move in the offseason before
Carlos Ascues scored his first goal as a Lion since joining in 2018. On August 10, the team earned a 1–1 draw against
Toronto FC before returning to Orlando for a midweek game against
Sporting Kansas City, winning 1–0. On August 17, Orlando visited
Allianz Field for the first time to play
Minnesota United FC, coached by former Orlando head coach
Adrian Heath. Minnesota scored a stoppage time equalizer in the 1–1 draw after a
Nani penalty had put Orlando ahead. At the end of the gameweek, Orlando had moved back up to eight place in the conference. However, two shutout losses to
Atlanta United FC and
San Jose Earthquakes to end August saw the team drop back down to ninth.
September On September 7, Orlando City hosted
Los Angeles FC who remained 11 points clear at the top of the
Supporters' Shield standings, earning a point in a 2–2 draw despite again leading late in the second half. On September 14, with only four games left in the season, Orlando faced playoff rivals
New England Revolution who were four points ahead of Orlando and occupying the final playoff spot heading into the game. Despite trailing 3–1 at halftime, Orlando fought back to score two unanswered goals and earn a 3–3 draw.
Nani was involved in every goal, scoring twice and registering one assist to set a new team record in single-season goal involvements with 21. However, a win for
Chicago Fire pushed Orlando down to tenth while they still remained four points behind New England. On September 21, Orlando traveled to face
Houston Dynamo. Having taken the lead through a sixth minute
Dwyer goal, their earliest goal of the season, Orlando had the potential to move back up the eighth and back within two points of the playoffs were they to hold on to the lead as both New England and Chicago had tied in their earlier matches. However, two unanswered second half goals for Houston meant Orlando lost 2–1, keeping them in tenth. On September 29, Orlando's final away game of the season and the team's first trip to
FC Cincinnati, ended in a 1–1 draw. The result, coupled with New England's victory over NYCFC, officially eliminated the team from playoff contention with one regular season game left. Benji Michel's goal was the 75th goal FC Cincinnati had conceded in 2019. It broke the MLS record for
most goals conceded in a single season set the previous year by Orlando City.
October Orlando City had the opportunity to leapfrog
Chicago Fire on the final day of the season but lost 5–2 to Chicago at home, keeping the team 11th in the Eastern Conference, 22nd in the
Supporters' Shield standings and taking their winless streak to eight to end the season. The following day the club announced they had parted ways with
James O'Connor. == Roster ==