Fungi historically placed in the iconic genera of Boletus, Leccinum and Xerocomus have been the subject of major taxonomic revisions in recent years. Yet, despite all advancements in systematics, boletoid fungi in insular ecosystems remain little explored and our knowledge of their diversity, distribution and abundance in Mediterranean ecoregions is far from complete. To shed light on this blind spot, the findings of a ten-year study from the island of Cyprus were analysed, integrating phylogenetic, ecological, morphological, phenological and chorological data. An unexpected diversity of Boletaceae fungi is unveiled, with twenty-five species phylogenetically confirmed to be present on the island, thirteen of them previously unreported. Sequencing of the ITS rDNA region, reveals crypticism within the Butyriboletus fechtneri, Caloboletus radicans, Rubroboletus lupinus and Rheubarbariboletus armeniacus species-complexes and infrageneric relationships are discussed. A strong link between boletoid fungi and Mediterranean oaks of the ilicoid group (Quercus alnifolia, Quercus coccifera subsp. calliprinos) is illustrated, with nineteen species (76%) overall found to be strictly or broadly associated with evergreen oaks. In stark contrast, the semi-deciduous Quercus infectoria subsp. veneris appears to be an unfavorable host for boletoid fungi, with just a single associated species so far. Phenological and chorological records indicate that most species on the island are rare, highly localized and fruit during very brief spells several years apart, mainly in response to increased annual, late summer or early autumn precipitation. The conservation status of these high-profile fungi is hence discussed, particularly in view of alarming climate changes, forecasted to have a dramatic impact on Mediterranean ecosystems in the years to come.