Kaká, who also became the team's first Designated Player after his release from AC Milan, was immediately loaned to São Paulo until the start of the MLS season.

[14] As part of that partnership, Orlando City later signed two players from Benfica U19s  – Estrela and Rafael Ramos – to MLS contracts on August 7, 2014.

[15] On November 21, 2014, head coach Adrian Heath signed a contract extension committing him to the club until the end of the 2017 MLS season.

[19] On March 21, Orlando conceded a late stoppage time goal to Octavio Rivero of Vancouver Whitecaps FC for their first defeat.

[20] In their inaugural season Orlando City finished 7th in the Eastern Conference and 14th in the overall standings, falling short of the playoffs by one point.

[26] However, O'Connor only managed two wins in his 18 games in charge in 2018 as City missed the playoffs for the fourth consecutive season and also set a new MLS record with 74 goals conceded on the year.

[28] Ahead of the 2020 season, Orlando hired former Colorado Rapids and FC Dallas head coach Óscar Pareja.

[29] With the season disrupted due to the COVID-19 pandemic, Orlando competed in the MLS is Back Tournament held at the ESPN Wide World of Sports Complex in July and August.

[31] After failing to make the postseason the previous five years, Orlando snapped the joint second-longest MLS playoff drought in history under the guidance of Pareja.

The Lions reached the conference semi-finals, eliminating New York City FC in a dramatic penalty shootout in the first round before losing to New England Revolution.

On May 12, 2021, Orlando City majority owner Flavio Augusto da Silva announced he was in advanced negotiations with Zygi and Mark Wilf, owners of National Football League franchise Minnesota Vikings, for the sale of the club including the Orlando Pride, Exploria Stadium, and other related soccer assets.

[34] On September 7, 2022, Orlando City won their first trophy as an MLS team, beating USL Championship side Sacramento Republic 3–0 in the 2022 U.S. Open Cup final.

[40] In round one, Orlando faced Canadian-side Cavalry FC, and defeated them 6–1 on aggregate, the first time the club had won in the competition.

[47] However, in May, the Florida House of Representatives failed to vote on a bill that had passed the Senate that would have provided up to $30 million in state funds towards the stadium project.

Cyle Larin scored the first goal in stadium history as Orlando City won 1–0 in front of a sellout crowd of 25,550.

On October 6, 2017, the stadium hosted the United States men's national team for the first time in a 2018 FIFA World Cup qualifier against Panama.

[58] On June 4, 2019, the naming rights to the stadium were sold to Florida-based time share and vacation rental company Exploria Resorts.

[61][62] Prior to the completion of Orlando City's soccer specific stadium, the Lions occupied the then-named Citrus Bowl for their first two seasons in MLS, which the team had also invested in for renovations.

In the opening home matches of the 2015 and 2016 seasons, Orlando City ran their "fill the bowl" campaign, which led to sell-out crowds of over 60,000.

[68][69] In OCB's absence in 2021, Orlando City resurrected their under-23 team to play in the developmental United Premier Soccer League.

The stated goal of the program is to "share the joy of the game" while simultaneously "developing their skills and promoting healthy sportsmanship".

[75] It was a vision first set out by the club's executive vice president of soccer operations, Luiz Muzzi, upon his appointment in December 2018 as a means of solidifying the in-house pipeline from youth to professional.

The main aspects, including the purple color scheme and lion ident, carried over from the logo of the USL Pro team.

The logo consists of a gold Lion face with 21 sun flares making up its mane sitting within a purple shield.

The number of flares represents the club's position as the twenty-first team in MLS, while the sun-shaped mane is in reference to Florida's nickname as The Sunshine State.

[85][86] The club has two major active supporters groups, which combine forces on game days to create "The Wall" now housed in the safe standing section: The Ruckus and The Iron Lion Firm.

[91] From the beginning, the series has seen several fan incidents as well as player and front office animosity including both teams banning the others' supporters groups.

Nevertheless, the two teams made their MLS debut against each other with 10-man Orlando rescuing a dramatic 1–1 draw in stoppage time, and used each other as a bench mark in that first campaign.

Tensions peaked when the two teams met in the 2020 MLS Cup Playoffs, a chaotic game that saw NYCFC's season end in farcical fashion and re-established Orlando's status as a rival in the eyes of New York City fans.