Chiral cyclopropyl- and cyclobutylboronic esters and -silanes have become attractive intermediates for the preparation of functionalized small rings. This review highlights the stereoselective methods developed for their preparation, including both diastereo- and enantioselective approaches. 1 Introduction 2 Stereoselective Synthesis of Cyclopropyl- and Cyclobutylboronates and -silanes 2.1 Diastereoselective Synthesis of Cyclopropyl- and Cyclobutylboronates and -silanes 2.2 Asymmetric Synthesis of Cyclopropyl- and Cyclobutylboronates and -silanes 3 Conclusions