This review covers preparative-scale chromatography for enantioseparations in both supercritical fluid and liquid chromatography published between 2016 and 2020. When pertinent, some fundamental publications from outside this time window are cited. The recent developments in instrumentation, novelties in method development and chiral stationary- and mobile phases are placed in context, while throughput, scale-up and sample issues are presented for supercritical fluid chromatography, and large-batch techniques together with computer-assisted method development, are described for liquid chromatography. Preparative-scale applications are reported for natural products, pharmaceutical compounds and pesticides, as well some other small molecules. Finally, a section is devoted to reports comparing supercritical fluid- and liquid chromatography and the strategies of various commercial users are briefly described. The goal of this review is to present current practices in the field of medium to large-scale chiral separations and offer indications as to how the best approach may be chosen for a given application.