Photos from the event show both singers enjoying themselves in the same carnival booth.
This meeting comes just months after they connected at a Fenty Beauty show in London.
The Crop Over Festival is a three-month celebration of Barbadian music, arts, food, culture, and more.
Since its inception in 1974, it has become an annual event aimed at attracting tourists to the island and preserving local folk culture.
The festival usually begins in June and culminates on the first Monday in August with a grand carnival parade known as Kadooment Day, which is considered the biggest Caribbean carnival.
