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Microbial natural products (MNPs) have been identified as important hotspots and effective sources for drug lead discovery. The genus <i>Phaeosphaeria</i> (family: Phaeosphaeriaceae, order: Pleosporales), in particular, has produced divergent chemical structures, including pyrazine alkaloids, isocoumarins, perylenequinones, anthraquinones, diterpenes, and cyclic peptides, which display a wide scope of biological potentialities. This contribution comprehensively highlights, over the period 1974&#8315;2018, the chemistry and biology of the isolated natural products from the micro-filamentous <i>Phaeosphaeria</i> fungi genus. A list of 71 compounds, with structural and biological diversities, were gathered into 5 main groups.