in the 2019 NBA draft, Cannady joined the Oklahoma City Thunder at 2019 NBA Summer League. On October 15, 2019, he signed with the Brooklyn Nets of the NBA, four days before being waived by the team prior to the regular season. On October 27, Cannady was allocated to Brooklyn's NBA G League affiliate, the Long Island Nets. During Cannady's rookie season, he had to balance playing professional basketball with completing his sociology degree from Princeton. On December 27, he scored a career-high 33 points along with eight rebounds and three assists in a 109–95 win over the Erie BayHawks. Through 40 games with Long Island in the 2019–20 season, Cannady averaged 14.4 points, 3.9 rebounds and 2.6 assists per game. Lakeland Magic (2021) On November 27, 2020, Cannady signed with the Orlando Magic, but was later waived by the Magic on December 19 after appearing in two preseason games. On January 24, 2021, Cannady was included in roster of the Lakeland Magic where he played in 13 games and averaged 11.7 points, 2.8 rebounds and 2.7 assists in 25.8 minutes, while shooting .400 from three-point range. The Lakeland Magic won the G League championship in the shortened single-site 2021 season in Orlando and Cannady was named the championship game most valuable player after scoring 22 points in the final. Orlando Magic (2021) On April 6, Orlando signed Cannady to a 10-day contract, but on April 13, he was waived after three games. Three days later, he signed a two-way contract with the Magic. On April 25, Cannady suffered a compound fracture to his right ankle during a 131–112 loss to the Indiana Pacers. On May 4, he was waived by Orlando. Return to Lakeland (2021–2022) On October 12, 2021, Cannady signed with Orlando for his second stint with the team. However, he was waived three days later. Cannady subsequently rejoined the Lakeland Magic. Return to Orlando (2022) On March 31, 2022, Cannady signed a 10-day contract with the Orlando Magic and on April 10, he signed for the rest of the season. Cannady was waived prior to the start of the 2022–23 season. South Bay Lakers (2022–present) On November 3, 2022, Cannady was named to the opening night roster for the South Bay Lakers. Career statistics Regular season |- | style="text-align:left;"| | style="text-align:left;"| Orlando | 8 || 0 || 9.3 || .393 || .375 || .857 || .6 ||