Four novel cobalt(II) complexes with the non-steroidal anti-inflammatory drugs - fenamic acid derivatives have been synthesized and characterized. The complexes [Co(neo)(fen)2] (1) and [Co(neo)(tol)2] (2) were prepared by the reaction of fenamic (Hfen = 2-(phenylamino)benzoic acid) and tolfenamic acid (Htol = 2-[(3-chloro-2-methylphenyl)amino]benzoic acid), respectively with cobalt(II) chloride and neocuproine (neo = 2,9-dimethylphenantroline). However, the same procedure applied to niflumic acid (Hnif = 2-{[3-(trifluoromethyl)phenyl]amino}nicotinic acid) mixture has led to formation of [Co(neo)(nif)2(MeOH)]·MeOH (3A) and [CoCl(neo)(nif)(MeOH)] (3B). The crystal structure of all prepared compounds has been determined by single-crystal X-ray crystallography. Complexes 1 and 2 were further subjected to full spectral characterization (IR, UV-VIS, fluorescence) as well as biological activity studies. The radical scavenging activity against free model radicals ABTS (diammonium 2,2’-Azino-bis(3-ethylbenzothiazoline-6-sulfonate) and DPPH (2,2-Diphenyl-1-picrylhydrazyl) revealed the selectivity of complexes against ABTS with higher scavenging activity observed for 2, while both compounds were ineffective towards DPPH. Furthermore, the interaction of molecules with Fish-sperm DNA revealed a moderately strong interaction based on combined intercalative and minor-groove binding mode. The interaction with human and bovine serum albumins determined by fluorescence quenching experiments revealed the binding constants within the optimal range proposed for effective drug binding.