Grand Slam debut

Kenin made her junior Grand Slam debut in 2014, but only recorded one match win in singles while playing in the latter three events of the year. Following the US Open, Kenin represented the United States at the Junior Fed Cup alongside CiCi Bellis and Black. The team won the tournament, sweeping Slovakia 3–0 in the final. Kenin went undefeated in her five matches, all in doubles. Her next breakthrough came towards the end of the year when she won the Orange Bowl, defeating Bellis and Ingrid Neel in the last two rounds.