The 2014 season was a step back on the track for Cheptai, as she finished lowly in Diamond League races and failed to improve her bests. She did make progress in road running, however, coming second at the Groningen Four-Mile Run and Nairobi Diamond 10K Run, setting a best of 31:45 minutes at the latter. She began training with Turkish athletics club Üsküdar Belediyesi and brought the club victory in the individual and team categories at the European Champion Clubs Cup Cross Country. After winning the Discovery Kenya Cross Country, Cheptai was again selected for the Kenyan team for the 2015 IAAF World Cross Country Championships and reached a new high in seventh place, winning the team silver medals with Kenya. On the 2015 IAAF Diamond League circuit, she placed in the top six of the 5000 m at the Shanghai Golden Grand Prix, Prefontaine Classic and Bislett Games. A runner-up finish to Viola Kibiwott at the 2015 Athletics Kenya World Championship Trials earned her a place on her first senior track team for Kenya.