Eleven novel 1,2,4-triazolylbenzotriazoles have been prepared using 1-(hydrazinylcarbonylmethyl)-1 H -benzotriazole (3) as a potent intermediate. Compound 3, however, was obtained from benzotriazole in two steps. All synthesized compounds were characterized by detailed spectral studies like IR, H-1 NMR, C-13 NMR, and mass spectrometry. All synthesized compounds were evaluated for their in vitro antimicrobial activity against seven strains of bacteria and four strains of fungi. Compounds 13, 17, 19, 20, and 21 were found to possess antibacterial activity comparable to that of ciprofloxacin against a Klebsiella pneumoniae strain. Except for compounds 2 and 13, all compounds showed good antifungal activity against an Aspergillus niger strain as compared to miconazole. The synthesized compounds were also evaluated for their antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay and the results are encouraging, especially for compounds 3, 20, and 21.