The rapid emergence of organic (opto)electronics as a promising alternative to conventional (opto)electronics has been achieved through the design and development of novel π‐conjugated systems. Among various semiconducting structural platforms, 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) π‐systems have recently attracted attention for use in organic thin‐films transistors (OTFTs) and organic photovoltaics (OPVs). This Review article provides an overview of the developments in the past 10 years on the structural design and synthesis of BODIPY‐based organic semiconductors and their application in OTFT/OPV devices. The findings summarized and discussed here include the most recent breakthroughs in BODIPYs with record‐high charge carrier mobilities and power conversion efficiencies (PCEs). The most up‐to‐date design rationales and discussions providing a strong understanding of structure‐property‐function relationships in BODIPY‐based semiconductors are presented. Thus, this review is expected to inspire new research for future materials developments/applications in this family of molecules.