At the World Athletics Championships, Cheruiyot won the silver medal in 2017 in London, and a gold in 2019 in Doha.

Beginning in 2014, he began to train in the outskirts of Nairobi, via the Rongai Athletics Club, under Coach Bernard Ouma.

[4] Cheruiyot would have a rematch against Blankenship three weeks later at the Prefontaine Classic in Eugene, Oregon, in the men's International Mile.

[7] He also took a silver medal in the 1500m at the African Championships in Durban (3:39.71), and finished 2nd in the Emsley Carr Mile (3:53.17) at the Anniversary Games in London.

[2] Although disappointed by not making Kenya's Olympic Team, Cheruiyot had another breakthrough by winning the 1500 m at the Brussels Diamond League, in a personal best time of 3:31.34.

[12] At the aforementioned World Championships, Cheruiyot won the silver medal, finishing behind compatriot Elijah Manangoi.

[14][15] At the Commonwealth Games held on the Gold Coast, Cheruiyot claimed the silver medal in the 1500 m. On 12 May, he won the Shanghai Diamond League in a time of 3:31.48.

[31] However, he was allowed to compete as second-placer Kamar Etyang was barred for participating due to not meeting anti-doping rules.

[51] At the Oslo Diamond League on 30 May, Cheruiyot finished second, being narrowly pipped on the line by a diving Jakob Ingebrigtsen, in a season's best of 3:29.77.

[55] At the 2024 Summer Olympics in Paris, Cheruiyot finished 11th in the 1500 m, having tried to go with the early pace he faded badly over the last lap.

[56] He recovered from his dissapointment to win over 800 m at the Grand Prix Lombardia in Brescia and finish second over 1500 m at the Diamond League Final in Brussels.

[57][58] In November, Cheruiyot expressed his desire to retire from the 1500 m after the 2025 World Championships in Tokyo, and transition to long-distance running and marathons.