Orlando City
On February 15, 2022, Orlando City signed Freeman to a four-year homegrown contract with an additional option year having spent preseason with the first-team, making him the club's 12th homegrown signing. Freeman made his first senior appearance on March 26, in the reserve team's first MLS Next Pro match when he started in a 2–0 victory over Chicago Fire II. Freeman would finish the 2022 campaign with Orlando City B with 19 appearances and three assists.
On March 31, 2023, Freeman scored his first professional goals when he netted a brace in a 2–1 victory over new expansion side Huntsville City in a match for Orlando City B. On April 29, 2023, Freeman made his debut for the club when he came on as a 93rd-minute substitute for Michael Halliday in a 2–0 victory over LA Galaxy. Freeman made his MLS Next Pro playoffs debut on October 1 when he came on as a 95th-minute substitute for Dominic Pereira in a 2–1 quarterfinals loss to Columbus Crew 2. Freeman would finish the 2023 season with Orlando City B with 25 appearances, four goals, and three assists.
On July 6, 2024, Freeman made his first goal contribution for the senior team after he came on as an 82nd-minute substitute for Kyle Smith against D.C. United. Freeman passed the ball to Ramiro Enrique from a redirected Nicolás Lodeiro free-kick, and Enrique scored to help the game end 5–0 in Orlando's favor. On September 8, Freeman made his first triple goal contribution when he scored two goals and assisted in another in a 4–1 victory at Crown Legacy FC. Later, on September 25, Freeman was named MLS Next Pro Player of the Matchweek for contributing two assists in a 3–0 win over Chicago Fire II two days earlier, helping to clinch the playoffs. Freeman's performances throughout the month of September also saw him voted MLS Next Pro Player of the Month for the first time. On October 20, Freeman started his first playoffs game in a 1–1 draw at Chicago Fire II, which then went into a penalty kick shootout. Freeman took Orlando's first penalty and successfully converted it, but Orlando would go on to lose the penalty kick shootout 5–4. Freeman finished the 2024 campaign with Orlando City B with 26 appearances, eight goals, and nine assists, the most assists and total goal contributions on the team.
On March 1, 2025, Freeman made his first career start for the club in a match against Toronto FC, and in the 35th-minute through an assist from Kyle Smith, he scored his first goal for the club. Freeman's goal helped the match end 4–2 in Orlando City's favor. For his performance, Freeman was named to the bench of the Team of the Matchday for the first time in his career two days later. On March 22, Freeman assisted in Luis Muriel's opening goal in a 4–1 win over D.C. United and later he scored the third goal of the match when he headed a free kick from Martín Ojeda. Freeman's performance would see him named to the starting Team of the Matchday for the first time in his career two days later.
On June 25, Major League Soccer announced Freeman had been voted in to represent the league in the 2025 MLS All-Star Game against the Liga MX All-Stars on July 23 at Q2 Stadium in Austin, Texas. Freeman's selection to the All-Star team made him the youngest player to ever be picked for the exhibition match. On July 15, Freeman was selected to represent the league in the MLS All-Star Touch Challenge during the MLS All-Star Skills Challenge a day before the game. Liga MX All-Stars defeated the MLS All-Stars in the All-Star Touch Challenge, but the MLS All-Stars won 4–2. Freeman also participated alongside YouTube and Twitch star IShowSpeed in the Shooting and Passing challenges. MLS All-Stars would also ultimately defeat the Liga MX All-Stars 3–1 in the All-Star Game with Freeman coming on as a 61st-minute substitute for Orlando City teammate Marco Pašalić.
On September 13, Freeman scored the equalizing goal in a 1–1 draw at D.C. United when he headed a rebounded shot from Pašalić into goal. After heading the ball, Freeman was struck in the head by a high boot from Lukas MacNaughton, who was sent off with a red card as a result. As a result, Freeman was named to the Team of the Matchday for the second time in his career. Freeman was again named to the Team of the Matchday for scoring another late equalizing goal, this time against FC Cincinnati on September 28, to secure a 1–1 draw. Freeman placed second in the 2025 22 Under 22 rankings with 1,220 points, only behind Seattle Sounders' Obed Vargas, who had 1,231 points. Freeman was named the MLS Young Player of the Year ahead of Vargas and Real Salt Lake's Diego Luna and became the first player in team history to be named to the MLS Best XI. In Freeman's breakout season, he registered six goals and six assists across all competitions for a total of 12 goal contributions. The club exercised Freeman's contract option after the conclusion of the season, which would see him contracted to the club through the 2026 season.
