Cutting characteristics of thin membranes and the mechanics of their interactions with sharp aggressors like needles are critical in many industrial and medical applications. In this study, we performed needle insertion experiments to study the cutting behaviour of membranes made with polyethylene (PE) and nitrile butadiene rubber (NBR) and investigated different stages of the procedure by analyzing the needle reaction force. Moreover, using a detailed parametric study, we investigated the effect of different insertion and membrane parameters on the most important features of the insertion process. The results showed that, in most cases, the crack size, maximum insertion force, puncture displacement, kinetic frictional force, and static frictional force increase with the increase of needle diameter, increase of membrane thickness, or inclining of the needle. On the other hand, the effect of the velocity on features of the insertion process is negligible except for the kinetic frictional force which increases with the insertion velocity. We also showed although lubrication cannot considerably change the maximum needle insertion force into thin membranes, it can substantially decrease the puncture displacement and frictional forces. Furthermore, we observed that the maximum insertion force, puncture displacement, and frictional forces for PE are greater than the values obtained for NBR, while the crack sizes obtained for PE are smaller than those for NBR. Additionally, we proposed a combined experimental-numerical approach using finite-element (FE) modelling to calculate fracture toughness. The fracture toughness values obtained for PE and NBR are 6.66 ± 1.16 kJ/m2 and 3.98 ± 0.56 kJ/m2, respectively. We also exploited the developed finite-element model to predict the whole-field membrane deformation and its mechanical stress.