In the last few years, many microfungi—including plant-associated species—have been reported from various habitats and substrates in Italy. In this study of pleosporalean fungi, we researched terrestrial habitats in the Provinces of Arezzo (Tuscany region), Forlì-Cesena and Ravenna (Emilia-Romagna region) in Italy. Our research on Italian pleosporalean fungi resulted in the discovery of a new species, Italica heraclei (Phaeosphaeriaceae). In addition, we present a new host record for Pseudoophiobolus mathieui (Phaeosphaeriaceae) and the second Italian record of Phomatodes nebulosa (Didymellaceae). Species boundaries were defined, based on morphological study and multi-locus phylogenetic reconstructions using Maximum Likelihood and Bayesian Inference analyses. Our findings expand the knowledge on host and distribution ranges of pleosporalean fungi in Italy.