This study evaluated of the role of library associations of the English Speaking Caribbean with specific focus on the Library Associations of Trinidad and Tobago and Jamaica. Forty ? two members from each association made up the sample for this study which consisted of forty members responding to questionnaires and an interview with the President from each association. Content analysis of some of the reports of these library associations was done to gather pertinent data. The research has a qualitative design and so the data was analysed using a descriptive and explanatory approach. The findings indicate that in spite of numerous challenges, the library associations of Trinidad and Tobago and Jamaica attempt to fulfil their respective roles and obligations to the profession by providing Continued Professional Development opportunities and promoting the image of the association. The study also reveals that these associations suffer from a lack of financial viability, recognition from government and participation from membership.