Ten novel 2-aryl-5-(arylsulfonyl)-1,3,4-oxadiazoles were produced and assessed for their in vitro antibacterial and antioxidant activities. Diverse spectroscopic methods like 1H NMR, 13C NMR, IR, and LCMS were used for the characterization of the prepared samples and all the data was in good agreement with the anticipated structures. The prepared compounds 6a-j were screened for their in vitro antibacterial activity against bacterial strains Pseudomonas aeruginosa, Enterobacter aerogenes, Escherichia coli (gram-positive), and Bacillus cerus, Staphylococcus aureus, Bacillus subtilis (gram-negative). The antimicrobial screening outcome revealed that the prepared 2-(3,4-dimethylphenyl)-5-tosyl-1,3,4-oxadiazole (6j), 2-(3-isopropylphenyl)-5-tosyl-1,3,4-oxadiazole (6c), and 2-(2-ethylphenyl)-5-tosyl-1,3,4-oxadiazole (6i) are most potent among all the examined compounds. Furthermore, the antioxidant activity of the prepared compounds was also investigated by DPPH radical scavenging method and the results showed that some of the compounds were moderately active.