For the first time, a thiosemicarbazone-type ligand containing a paracetamol structural unit was synthesized. Five new coordination compounds based on copper(II) salts: [Cu(L)CH₃COO] (1), [{Cu(L)Cl}₂]·H₂O (2), [Cu(L)H₂O·DMF]NO₃ (3), [Cu(L)Br] (4), [Cu(L)H₂O]ClO₄ (5), were obtained, where HL is N-[4-({2-[1-(pyridin-2-yl)ethylidene]hydrazinecarbothioyl}amino)phenyl]acetamide. The new HL was characterized by NMR, FTIR, spectroscopy, and X-ray crystallography. All copper(II) coordination compounds were characterized by elemental analysis, FTIR, EPR spectroscopy, and molar electrical conductivity. Furthermore, single crystal X-ray diffraction analysis elucidated the structures of thiosemicarbazone HL as well as complexes 1–3. All compounds were tested for antimicrobial, antifungal, and antioxidant activities, and their toxicity to Daphnia magna was studied. Biological evaluation has revealed that most of the synthesized compounds demonstrate promising antibacterial, antifungal, and antioxidant activities. In many cases, their antibacterial/antifungal activity is comparable to that of certain drugs used in medicine for these purposes, and in some cases, even surpasses them. HL and complexes 2–5 exhibit antioxidant activity that surpasses that of Trolox. Furthermore, HL and complex 2 display virtually no toxicity to D. magna.