Italy is a Mediterranean country in south-central Europe that has a long tradition in mycology. The mycological journey from ancient Italy to modern advanced studies is remarkable. In this study, we outline historical studies on different fungal groups, mycologists’ contributions, fungal collections, illustration techniques, and their development, including traditional and modern taxonomic approaches. In addition, the current progress of mycology is discussed, with an emphasis on plant-associated Ascomycota. Furthermore, a case study was carried out to better understand the occurrence of saprobic Ascomycota on different host plants in terrestrial habitats. We describe a novel genus, Pigmentatineomassaria (Neomassariaceae, Pleosporales), with the type species, P. italica, and another novel species, Alborbis italica (Sydowiellaceae, Diaporthales) as well as 16 novel host records, five new geographical records, two new regional records, and two host recurrent species, from Botryosphaeriaceae, Melanopsaceae (Botryosphaeriales), Hysteriaceae (Hysteriales), Cucurbitariaceae, Didymellaceae, Leptosphaeriaceae, Melanommataceae, Nigrogranaceae (Pleosporales) in Dothideomycetes and Cytosporaceae (Diaporthales), Nectriaceae (Hypocreales), and Graphostromataceae, Diatrypaceae (Xylariales) in Sordariomycetes. Identifications are based on detailed morphologies, descriptions, and updated multi-gene phylogenetic analyses, including ecological and mycogeographical data. To evaluate the mycological progress of plant-associated Ascomycota during the past decade, study-based data analyses and mapping were performed by focusing on the database of Italian microfungi (https://italianmicrofungi.org/) webpage. The present study provides an overview of Italian mycology and inspires mycologists to explore the hidden fungal diversity in poorly observed natural Italian forest ecosystems. Also, this work paves the way for advanced fungal taxonomy based on a polyphasic approach and promotes ecological and mycogeographical data documentation in Italy as well as in other Mediterranean countries.