Interfacial bonding between fibre and matrix is most critical to obtain enhanced mechanical properties of the resulting composites. Here we present a new surface tailoring method of selective wet etching and organosilicon monomers (3-(Trimethoxysilyl) propyl methacrylate, TMSPMA) deposition process on the short S-Glass fibre as a reinforcing material, resulting in increased mechanical retention and strong chemical bonding between glass fibres and polymer resin (a mixture of triethylene glycol dimethacrylate (TEGDMA) and urethane dimethacrylate (UDMA) monomers). The effect of surface modification on fibre matrix interfacial strength was investigated through microdroplet tests. An S-Glass fibre treated with piranha solution (a mixture of H2O2 and H2SO4) for 24 hours followed by TMSPMA surface silanization shows highest increase up to 39.6% in interfacial shear strength (IFSS), and critical fibre length could be reduced from 916.0 µm to 432.5 µm. We find the optimal surface treatment condition in that the flexural strength of dental composites reinforced by the S-Glass fibres enhanced up to 22.3% compared to the composites without fibre surface treatments. The significant elevation in strength is attributed to changes in the surface roughness of glass fibres at atomic scale, specifically by providing the multiplied spots of the chemical bridge and nano-mechanical interlocking. The findings offer a new strategy for advanced tailoring of short S-Glass fibres to maximise the mechanical properties of biomedical and dental composites.