[4] Another notable departure was Cristian Higuita who had been the sole remaining member of the team's inaugural MLS roster in 2015 and departed as the club's leading appearance maker with 108 across all competitions.

[10][11] The team also did a significant amount of recruiting in South America, bringing in Colombian midfielder Andrés Perea, Argentine defender Rodrigo Schlegel and Brazilian defender Antônio Carlos all on one-year loans from Atlético Nacional, Racing Club and Palmeiras respectively while Brazilian midfielder Júnior Urso joined permanently from Corinthians.

The game was also notable for the substitute appearance of on loan Andrés Perea who became the first person born in the 21st century to play for Orlando City SC.

It ended in a 2–1 defeat to Colorado Rapids as Drew Moor headed a 90th-minute winner from a corner after substitute Chris Mueller had scored the team's first goal of the season to tie up the game in the 82nd minute.

[20] On March 12 it was announced that the 2020 Major League Soccer season had been temporarily suspended for 30 days on the advice of public health authorities due to the COVID-19 pandemic.

[27] The result, coupled with Philadelphia Union beating Inter Miami later that evening, meant Orlando sealed qualification to the knockout round with a game to spare.

João Moutinho forced the shootout, scoring an equalizer against his former club off a Nani corner in the 90th minute, his first goal for Orlando City.

[34] On August 19, following the return of the MLS regular season in home markets, Orlando City announced that all three phase one games at Exploria Stadium would be open to fans at a reduced capacity and that face coverings would be mandatory for those in attendance.

[35][36] Phase one consisted of Orlando playing three regional opponents both home and away: Inter Miami CF, Nashville SC and Atlanta United FC.

[42] On September 5, Orlando's second matchup with Atlanta inside a week ended in a 1–1 draw after Adam Jahn scored a stoppage time equalizer.

[43] After playing five games in a 15-day stretch, Orlando had a full week break before the final phase one match on September 12: Miami's first visit to Exploria Stadium.

[45] With the conclusion of the phase one home and away series, Orlando hosted Chicago Fire FC on September 19, winning 4–1 and equaling the club record streak of six games unbeaten in regular season MLS play in the process.

Johnny Russell halved the home team's deficit early in the second half but the Lions held out to also maintain the club's 100% win record when leading by two goals in MLS history.

[48] Orlando's first game of October saw the Lions play New York Red Bulls for the first time in 2020, a 3–1 home win that saw the first goal for the club by Antônio Carlos and the professional debut of homegrown player David Loera.

[49] With Gallese away on international duty, Brian Rowe made his first appearance of the season on October 7 as Orlando stretched the unbeaten run to 10 matches after a heavily rotated team played out a goalless draw away to Atlanta United.

[54] Despite conceding a 90+5-minute equalizer in a 1–1 draw with New York Red Bulls earlier in the evening,[55] Orlando City's first MLS playoff berth in club history was confirmed on October 18 with a combination of the tie and Toronto FC later beating Atlanta United 1–0 thanks to an 89th-minute winner by Pablo Piatti.

[57] Orlando's final game of October was a 4–1 win over Atlanta, the fourth meeting between the two teams on the season with the Lions remaining unbeaten in the series.

Orlando dominated the first half and led at half-time as Chris Mueller hit double figures for goals for the first time in his professional career.

The victory guaranteed Orlando a top-four finish in the Eastern Conference and home field advantage in the first round of the playoffs as a result.

[62] Having moved up to third place in the Eastern Conference with the victory over Columbus, Orlando just needed to avoid defeat against Nashville SC in the final game of the season to retain the #3 seed for the playoffs.

The Lions, who were unbeaten at home on the season coming into the game, took the lead early in the first half through Dike but were pegged back and went into half-time tied at 1–1.

Having re-established the lead with a Nani freekick on the hour mark, Nashville turned the game around late on with goals in the 88th and 90+3rd minute to win 3–2, handing Orlando their only home loss of the regular season.

However a VAR review deemed Gallese had left his goal line early which resulted in his second yellow card having been booked in extra-time for time wasting.

[69] As a result of the debacle, which gained international attention,[70][71] MLS suspended referee Allen Chapman and the rest of the officiating crew for the remainder of the playoffs.

[73] Orlando City reported for the start of preseason at their new training facility on January 20 before a closed-door friendly against Stetson University five days later.

Phase 1 schedule With the season disrupted by the COVID-19 pandemic two games in, Orlando did not return to in-market play until August 22 with a six-game home and away series against Inter Miami, Nashville SC and Atlanta United.

Inter Miami CF were predetermined as A2 prior to the draw taking place in order to make the first meeting between the two teams the tournament opener.

[87][88] On August 17, 2020, the United States Soccer Federation announced the cancelation of the U.S. Open Cup as a result of the coronavirus pandemic, the first time the tournament had not been played since its inception in 1914.