2017: Major debut Kypson made his Grand Slam main draw debut at the
2017 US Open after receiving a wildcard for winning the under-18 boys championship. In November 2017, Kypson won his first title on the
ITF Men's Circuit in
Niceville, Florida, beating
Sekou Bangoura in the final.
2023: French Open wildcard, Challenger title, top 200 Kypson received a wildcard for the
2023 French Open after winning the USTA's Roland Garros Wild Card challenge. In July, Kypson won his first
Challenger title in
Medellín, Colombia, beating
Benjamin Lock in the final.
2024: First ATP win & quarterfinal, top 150 & Masters debuts For his debut at the
2024 Australian Open, Kypson received a reciprocal wildcard, having won the 2024 USTA Australian Open Wild Card challenge. Ranked No. 155, he also entered as a wildcard at the
2024 Delray Beach Open and recorded his first ATP win with an upset over previous year runner-up and fifth seed
Miomir Kecmanović. As a result, he reached the top 150 in the rankings. Next he defeated
Constant Lestienne to reach his first ATP quarterfinal. He also received a wildcard for the
2024 BNP Paribas Open for his Masters 1000 debut, and recorded his first Masters win over qualifier and compatriot
Ethan Quinn.
2025: Four Challenger titles, top 125 In October, Kypson claimed his third
Challenger title of the season at the
2025 MarketBeat Open and returned to the top 150 in the singles rankings on 27 October 2025. As of 28 October, Kypson was again in the lead of the USTA competition, awarding the 2026 Australian Open WildCards. In November, Kypson reached his fifth
Challenger final of the season at the
HPP Open in Helsinki, where he defeated home crowd favorite
Otto Virtanen to lift his fourth Challenger title. As a result Kypson reached a new career-high ranking in the top 125 at world No. 117 on 10 November 2025 and clinched the 2026 USTA Australian Open wildcard. ==ATP Challenger and ITF Tour finals==