<p>Oxidation is a fundamental reaction in organic chemistry and represents a unique strategy to convert starting materials with low oxidation states to new compounds with high oxidation states. Asymmetric oxidation is regarded as the most straightforward protocol to prepare chiral oxides with high oxidation states and has played a crucial role in the fields of organic synthesis, material science and the pharmaceutical industry. However, previous studies typically focused on several specific substrates, such as alkenes, alcohols, and ketones, which have been well summarized in many reviews. Exploration of new substrate categories and reaction patterns remains a major challenge in this field. During the last decade, considerable progress has been made in non-enzymatic catalyzed asymmetric oxidations of C(sp³)‒H bonds and heteroatoms. These advancements have facilitated the creation of diverse chiral molecules exhibiting excellent chemoselectivity and stereoselectivity. In this review, we summarize the progress in catalytic asymmetric oxidation of C(sp³)‒H bonds and heteroatoms during the past decade, which would provide insights into challenging issues and enable future development.</p>