Abstract Four new species from Cuba are described in the genus Ocellularia , emphasizing the importance of the Caribbean for the diversification of lichen fungi and the level of unrecognized species richness in Ocellularia . Three of the new species belong in the O. bahiana group: O. coronata Lücking & Pérez-Ortega, differing from O. bahiana by the ridged to folded thallus, vertically ridged apothecia, and complex columella largely covering the disc; O. fuscospora Lücking & Pérez-Ortega, differing from O. urceolaris in the immersed to erumpent, columellate apothecia; and O. radiata Lücking, differing from O. bahiana in the complex, radiating columella filling the disc. In contrast, Ocellularia nigririmis Lücking & Pérez-Ortega is a species of the O. papillata morphodeme with immersed apothecia with a small, black-rimmed pore filled by a greyish black columella, and small ascospores. We also clarify the taxonomy and nomenclature of columellate taxa in the O. bahiana group and provide a key to all thelotremoid Graphidaceae with small, brown, (sub-)muriform ascospores. The new combination Ocellularia lunensis (Nagarkar & Hale) Lücking is proposed.