Cutting tool experiences rapid variation in thrust forces and torque during drilling of carbon fiber reinforced plastic and titanium (CFRP-Ti) stacks due to distinct materials characteristics, leading to complex wear mechanism. Existing tribotests fail to emulate the multifaceted contact situation of tool interacting with multi-materials simultaneously. This work presents a cost-effective modification using hybrid CFRP-Ti split-ring in cross-cylinder configuration to replicate contact situation during the drilling operation. The results showed a high coefficient of friction (COF) of ∼0.5 against Ti6Al4V and ∼0.21 against CFRP ring. Whereas, the test against CFRP-Ti split-ring showed cyclic COF variation, driven by complex synergistic wear mechanism that completely transformed the sliding contact. The modified tribotest results provide applicable estimation of COF variation and synergistic wear mechanism correlating well with WC-Co tool wear experienced in CFRP-Ti stacks drilling.