[2] With the options of several players declined at the end of the previous season,[3][4] Orlando City set its sights on the off-season to rebuild its roster.

[5] During this time, it was announced that Orlando City B had elected to not participate in the 2018 USL season,[6] sparking alarm in regards to the club's youth development and depth.

[11] By mid-January, attention shifted to forward Cyle Larin after images of him undergoing a medical with Beşiktaş J.K. were posted on the Turkish club's Twitter account.

[15] On January 29, it was announced that Orlando City had acquired midfielder Justin Meram from Columbus Crew SC in exchange for $1.05 million in allocation money plus an international roster spot.

Despite Joe Bendik making a penalty save early on, D.C. United opened the scoring in the 32nd minute with a Yamil Asad free kick.

The Lions maintained pressure throughout the second half and eventually equalized in stoppage time following a forward run by Jonathan Spector that set Stefano Pinho up for his debut goal, securing a point with a 1–1 draw.

This marked the first Orlando City appearances for Lamine Sané and Josué Colmán, who both came on as second half subs, as well as Sacha Kljestan.

The visitors were able to level the scoreline in the 82nd minute, but a shot from Scott Sutter that deflected off of Colmán made its way into the back of the net and secured City all three points in the club's first victory of the 2018 Major League Soccer season.

[22] On April 8, the Lions made team history by securing their first win from a 2-goal deficit, with Dwyer scoring the game-winning goal in the 87th minute for a dramatic 3–2 comeback victory against the Portland Timbers.

[26] Then, in yet another come-from-behind thriller and their fifth straight win to close out the month, Orlando City defeated the Colorado Rapids with a 2–1 scoreline at the high altitude of DSG Park.

[28][29] A new club record was reached as the "Cardiac Cats" opened the month of May with their sixth straight victory, and fourth when conceding the first goal, in a 3–1 result against Real Salt Lake.

Orlando City was later criticized by local authorities and news organizations for routinely condemning behavior without taking any significant action to decrease such incidents.

[34] A 2–1 defeat at home to the Chicago Fire extended the losing streak to three games to close out the month, as the Lions looked ahead to a 4-game, 12-day road trip with stops in New York, Miami, Vancouver, and Montreal.

[36] The club was able to turn things around in their first match of the 2018 U.S. Open Cup when they defeated NPSL side Miami United FC 3–0 with goals from PC, Stefano Pinho, and Dillon Powers.

[40] Under Bobby's leadership, and changing to a three-back formation that showed much-improved stability in the defense, the Lions were able to eke out a 1–1 win on PKs (4–2), against D.C. United in the Round of 16 in the U.S. Open Cup on June 20.

[50] Then, despite taking the lead three times, Orlando lost 4–3 away to LA Galaxy on July 29, a game in which Cristian Higuita broke Cyle Larin's club record 89 appearances.

[51] On August 3, Orlando City traded Justin Meram back to Columbus Crew SC for $750,000 in Targeted Allocation Money and a 2019 international roster slot.

Prior to the team's game against FC Dallas on October 6, Orlando were officially eliminated from playoff contention following Montreal's win over Columbus Crew earlier that day.

On October 28, the final day of the regular season, Orlando traveled to a New York Red Bulls side who were one of two teams with the potential to win the Supporters' Shield.

Orlando finished the season bottom of the Eastern Conference and, because of Colorado Rapids' decision day win, dropped to 22nd in the Supporters' Shield.

On November 26, 2018, 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.

[54] The day after, the club announced it had decided not to exercise the contract options of eight players: Joe Bendik, Richie Laryea, Tony Rocha, Chris Schuler, Jonathan Spector, Scott Sutter, Donny Toia and Jose Villarreal.

[63] Source: Match reports After the fourth round draw was held on May 24, Orlando City entered the 105th edition of the U.S. Open Cup on the road in South Florida, against Miami FC on June 6.

[84] Additionally, certain matches were streamed live on Twitter following the announcement of a three-year agreement between Major League Soccer and the social networking service.