"It was very windy on the race course, but I kept going," said Cheboi.
PHOTOS: 2018 Bay to Breakers race in San Francisco
Gabriel Geay from Tanzania won second place, with a time of 36:04 and Aaron Braun from the United States came in third place clocking in at 36:45.
The female winner of the race was Jane Kibii clocking in at 40: 31.
Both Cheboi and Kibii won Bay to Breakers in 2017.
RELATED: Nearly 40,000 run in Bay to Breakers race in San Francisco
This year's theme of Bay to Breakers was to be original and ABC7 News definitely saw that originality with creative costumes from twin squids, Sponge Bob and an endless army of super heroes. "I love Bay to Breakers! It's my 30th year running, I love the party," Phyllis Nabhan said.
Thousands of runners made the trek about seven miles from downtown San Francisco to the Great Highway, with top elite runners making it look easy.
Alaska Airlines sponsored the 12K journey from the Financial District to Ocean Beach. Organizers said at least 40,000 registered participants and 125,000 spectators attended the race.
Click here for a look back at recent Bay to Breakers stories, videos, and photos.