The experimental investigation focuses on the fretting fatigue performance of M24 high-strength bolt slip critical connections (SCC) under shear load, taking into account the influence factors of faying surface treatments and bolt tightened levels. A novel extensometer supporting device for measuring micro-displacement between connection plates is proposed. The μ-N curves are obtained. Three-dimensional surface morphology scanning and fracture morphology analysis are conducted on the specimens. The results showed that the SCC contact area can be divided into stick, partial slip, and gross slip, with distribution ranges determined for each zone. Meanwhile the fretting fatigue life decreases with the increase of μ and pre-tension. Finally, a prediction of fretting fatigue life is made based on a multiaxial fatigue critical plane model.