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The aim of this study was to compare the chemical composition, as well as antioxidant, anti-inflammatory, antiacne, and cytotoxic activites of various extracts of <i>Cephalaria gigantea</i> and <i>C. uralensis</i>. It is worth underlining that we are the first to characterize the composition and evaluate the biological properties of extracts from <i>Cephalaria gigantea</i> and <i>C. uralensis.</i> Thus, the LC-DAD-MS³ analysis revealed the presence of 41 natural products in studied extracts. The 5-<i>O</i>-caffeoylquinic acid, isoorinetin, and swertiajaponin were the main detected compounds. Among the tested samples, ethanol extract of the aerial parts of <i>C. uralensis</i> (CUE) possessed the most suitable biological properties. It exhibited moderate ability to scavenge free radicals and good capacity to inhibit cyclooxygenase-1, as well as cyclooxygenase-2. Moreover, CUE possessed moderate antibacterial activity against all tested bacterial strains (<i>S. aureus</i>, <i>S. epidermidis</i>, and <i>P. acnes</i>), and importantly, it was non-toxic towards normal skin fibroblasts. Taking into account the value of calculated therapeutic index (>10), it is worth noting that CUE can be subjected to in vivo study. Thus, CUE constitutes a very promising antiacne agent.