The new, unexpected bioactive bis‐hydrazone derivative (4) was obtained, in 74 % yield, by reacting two molar equivalents of pyrazole‐4‐carbaldehyde (1) with one molar equivalent of 2,5‐dihydrazineyl‐1,3,4‐thiadiazole (2). The compound was comprehensively characterized, including X‐ray single crystal, DFT calculations, and bioactivity assessments. Hirschfeld surface analysis confirmed the presence of hydrogen bonding interactions, particularly N−H⋅⋅⋅N and C−H⋅⋅⋅π interactions, which influence the overall crystal packing. The target bis‐hydrazone exhibited significant antimicrobial activity against multi‐drug‐resistant bacterial strains, with the largest activity against S.typhimurium with an inhibition zone of 17.1±0.6 mm and MIC 31.25 μg/mL. The compound also demonstrated significant cytotoxic effects on cancer cells, with a higher IC50 ratio of 134.43 μg/mL against the normal cell line Wi38 and the lowest IC50 value of 45.88 μg/mL against the cancer cell line Caco2. Molecular docking was carried out with estrogen receptor alpha (ERα) and sodium‐glucose transporter SGLT1, which are relevant to Mcf7 and Caco2 cancer cell lines, respectively. Docking suggests the presence of specific amino acids that may influence the binding affinity between the ligand and receptor active sites through residue overlaps in chains A for SGLT1 and B for Erα, offering the ligand as a promising anticancer consistent with the IC50 outcomes.