<p>Loosening of bolted joint is very commonly observed in bolted structures subjected to fluctuating load. In the present study, numerical and experimental investigations on comparison of loosening behaviour is presented for a novel design of a bolted joint – <i>Oppositely Threaded Stepped Bolted</i> (<i>OTSB</i>) joint. Some investigations on loosening of standard bolted joint and bolted joint with locknut are also presented for studying the loosening behaviour of the <i>OTSB</i> joint for relative understanding. All the three types of joints are subjected to cyclic transverse displacement of ± 1&#xa0;mm in the presence of a preload. Loss of preload due to loosening of the bolted joints is measured to study the extent of loosening at the end of ten displacement cycles. Numerical and experimental studies carried out for different bolt preload (<i>F</i>_<i>P</i>) and locking force (<i>F</i>_<i>L</i>) values. Numerical simulations are accomplished using ANSYS Workbench 19.2 software. Comparison of the experimental and numerical studies shows that the <i>OTSB</i> joint is very effective in prevention of loosening.</p>