Biosecure Bubbles have enabled the return of sports during the COVID-19 pandemic. West Indies Cricket was involved in the first international sporting event with a tour to England. The Caribbean Premier League (CPL) was the first Cricket League and was held in Trinidad and Tobago. Extensive planning and adaptation to local conditions were required, and all involved had to be constantly updated and provide consent. The English Bubble was “contained” in that all facilities resided within one area: hotel, training, and match facilities. Persons were moved from one geographical area into the bubble. The CPL Bubble was “Water in glove” in which it had to extend to different areas. A single hotel housed the cohort but separate training and playing locations required managed movement. Interactions between those in the Bubble and those outside had to be coordinated and separated. This review describes the functioning of the two Bubbles and highlights the differences between the two models. Both were predicated on cohort education, repeated testing, and adherence to social distancing and hygiene. Yet both differed significantly in their construct and execution.