[2] In 2016, as the nation's third ranked recruit, he committed to playing collegiate tennis for the Ohio State Buckeyes.

[8] Wolf made his Grand Slam main-draw debut at the 2016 US Open in the doubles event, partnering with John McNally.

[11] He turned pro after going 35–2 and earning Big Ten Player of the Year honors as a junior at Ohio State.

On September 22, Wolf made it to the finals of the Columbus 3 Challenger event, losing to Peter Polansky.

He beat fellow rising American Michael Mmoh in the round of 16 and top seed Emilio Gómez in the semifinals.

189 in the ATP singles rankings on November 18, 2019, after winning the 2019 Champaign Challenger, defeating Sebastian Korda in a tight two-and-a-half hour match.

As of August 2020, Wolf won four Challenger titles and was victorious in three of his last five events dating back to the previous season.

He was 14–2 with two titles during the first two months of 2020 before play was suspended due to the pandemic and made his top 150 debut on March 2, 2020, at World No.

[15] Wolf is only the third Ohio State Buckeye to reach the third round at the US Open after Francisco González in 1980 and Roger Smith in 1994.

[17] Ranked 209th at the 2022 Abierto Mexicano Telcel in Acapulco, Wolf reached the second round as a qualifier after defeating World No.

[25] He defeated qualifier Mikael Ymer in the semifinals to reach the first final of his career which he lost in straight sets to Félix Auger-Aliassime.

[26] At the 2023 Australian Open, Wolf reached the fourth round, defeating Jordan Thompson, 23rd seed Diego Schwartzman and Michael Mmoh before losing to fellow American Ben Shelton in five sets.

[28] He reached the third round of a Masters 1000 for the first time on his debut at the 2023 Italian Open (tennis), defeating 14th seed Hubert Hurkacz.

[32] In July, at the beginning of the American summer swing, he also entered the main draw at the 2024 Atlanta Open as a lucky loser.

He received a wildcard for the Citi DC Open in Washington and defeated lucky loser Zachary Svajda.