In July of 2019, Reynolds signed a two-way contract with the Bucks. He'd go on to see all his action during the 2019-20 season in the G League. There, with the Wisconsin Herd, he averaged 14.8 points, 5.2 rebounds and 1.5 assists in 37 appearances (all starts). Arguably his best overall performance of the season was Nov. 17 in a win over the Capital City Go-Go, where Reynolds recorded 24 points (10-15 FG, 4-7 3Pt), five rebounds, three assists and three steals. His single-game G League season highs were 27 points, 10 rebounds, four assists, three steals and two blocks.

After going unselected in the 2018 NBA draft after attending Tulane, Reynolds signed an NBA contract with the Timberwolves. He saw his first minutes Mar. 3 against the Wizards, totaling two points and one rebound in two minutes. Shortly after, Mar. 12 against the Nuggets, the rookie had his first double-digit scoring effort, racking up 12 points, a career-high two steals and a career-high two assists. He would go on to match that assist mark once more during the season -- Mar. 29 in a win over the Warriors. Reynolds had his next double-digit scoring effort Mar. 30 against the 76ers, recording 10 points, four rebounds, one assist and one block. His next double-digit scoring effort was his best performance, and last performance, of the season. It was Apr. 10 against the Nuggets, and Reynolds managed 19 points, a career-high six rebounds, one assist and no turnovers in 26 minutes. Overall, throughout the season, Reynolds shot 41.2 percent from three and 88.9 percent from the free-throw line, showing off his prowess as a jumpshooter. The rookie also spent time in the G League, where he appeared in 33 games (nine starts). There, with the Stockton Kings, he averaged 16.0 points, 4.2 rebounds and 1.2 assists.