Schiff bases and their transition metal complexes represent one of the most prolific and versatile classes of compounds in the fields of coordination chemistry and medicinal inorganic chemistry. Characterised by the presence of the azomethine (-C=N-) linkage formed through condensation of primary amines with carbonyl compounds, these ligands possess an exceptional capacity to coordinate with a wide range of metal ions, yielding complexes with markedly enhanced pharmacological properties relative to the parent ligands. The present review systematically surveys the literature spanning the past two decades on the synthesis, structural characterisation, and biomedical applications of Schiff base metal complexes. Multiple representative examples of Schiff base systems derived from diverse precursors, including aminoantipyrine, isatin, sulphonamides, thiosemicarbazides, and hydroxy-naphthaldehyde-are examined alongside their complexes with copper(II), cobalt(II), nickel(II), zinc(II), iron(III), manganese(II), and vanadium(IV). Key pharmacological activities discussed include antimicrobial action against both Gram-positive and Gram-negative bacteria and pathogenic fungi, anticancer cytotoxicity against human cancer cell lines, DNA binding and cleavage activities, antioxidant and SOD-mimetic properties, and anti-inflammatory effects. The review analyses structure-activity relationships, the role of metal centre geometry and oxidation state, and the mechanistic basis for enhanced potency upon complexation. Synthesis schemes and representative structures of key compounds are provided to facilitate understanding of the coordination chemistry involved. The review identifies important trends, gaps in current knowledge, and directions for future research aimed at translating these in vitro findings into viable drug candidates.