After receiving scholarship offers from 14 American universities,[3] Sakurai enrolled at Dartmouth College in 2017.[4] In his freshman year, he won the Ivy League Title with the team.[5] He scored his first goal on October 13, 2018, against the Penn Quakers.[6] In 2020, the season was postponed due to the COVID-19 pandemic, so Sakurai trained with a team in his native Japan four times per week.[7] During his time with the Big Green from 2017 to 2019, he scored two goals and added six assists in 47 appearances.[2]
With a number of Toronto FC II players unavailable for upcoming fixtures, Sakurai was called up to the squad in June 2016.[15] He made his professional debut on July 2, 2016, appearing for 14 minutes in a 3–0 defeat to Wilmington Hammerheads in the USL.[15] In doing so, he became the first ever Japanese player to feature competitively for Toronto FC II.[16]
In April 2021, he joined Ituano FC Yokohama, remaining until April 2022.[17][18]
In April 2022, he signed a professional contract with Toronto FC II in MLS Next Pro, returning to his former club.[2]
^Hiro, Hayashi (August 4, 2022). "トロントFCへ恩返しがしたい。プロサッカー選手・トロントFC 櫻井 功大さん(中編)|Hiroの部屋" [I want to give back to Toronto FC. Professional Soccer Player Toronto FC Kota Sakurai (Part 2) - Hiro's Room]. Torja (in Japanese).