Jamaica's Bolt kicked his 100-metre season off Wednesday with a less than impressive time of 10.09 seconds at the Truman Bodden Sports Complex.
Bailey-Cole, who finished with the same time, is one of Bolt's training partners. Antiguan Daniel Bailey finished third with a time of 10.23.
Bolt has been battling a hamstring problem but said that wasn't to blame for the slow time.
"It was just a bad race," he said. "I just have to go back and figure out with my coach what went wrong.
"I felt it (hamstring injury) slightly. It wasn't a bothering pain so I can't blame it on that."
In the women's events, American Carmelita Jeter became the first to finish in under 11 seconds in the 100 metres, winning with a time of 10.95.
Cayman Invitational: Usain Bolt wins 100m in photo finish
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