Purpose: To synthesize and characterize novel Schiff base-chitosan composites and determine their antimicrobial activity. Methods: Novel Schiff-base chitosan composites were synthesized by grafting polyvinylpyrrolidone and then replacing it with different aldehydes. The resulting composites were characterized using advanced analytical techniques, including thermogravimetric analysis (TGA), x-ray diffraction (XRD) studies and Fourier transform infrared spectroscopy (FT-IR). Results: The FT-IR results revealed that the Schiff-base chitosan was successfully produced during mixing and the crystallinity change of the samples was explained by the XRD patterns. Thermogravimetric analysis (TGA) of compounds A1, A3 and A4 showed weight loss of the compounds with the most significant weight loss observed in the fourth and final steps of the reaction. Analysis of the surface morphology of compounds A3, A5, and A6 by scanning electron microscopy (SEM), revealed multiple layers of sheets in the dark gray sections, as well as kinked and wrinkled portions. Compounds A2 – A6 exhibited biological activities against Gram-positive and Gram-negative bacteria as well as fungal species. Docking studies indicate that compound A6, with a binding affinity of -3.09, demonstrates antibacterial properties. Conversely, compound A2, with a binding affinity of -9.102, exhibited antifungal activity. Conclusion: The synthesized compounds possess higher antifungal potential due to the presence of benzene ring which enhances the binding affinity for antifungal activity while diminishing their antibacterial activity