Effective extraction of pillars in airleg stopes requires an understanding of the failure mechanism and stability of pillars. Pillars can be extracted efficiently and safely by replacing them with standing supports that can handle the roof load. However, most pillar extraction is conducted in flat dipping stopes which neglects the influence of the horizontal stress on pillar stability by increasing the sliding potential along planes. In this study, an effective pillar extraction simulation in an inclined airleg stope is conducted with an intent to recover 100% ore and leave the rooms supported with pillar replacements. Firstly, an empirical stability analysis is done to ascertain the direction and magnitude of the stress components acting on a pillar in an inclined stope. Thereafter a finite volume numerical simulation in FLAC 3D is performed to further determine the strength-stress ratio distribution and pressure on the pillars. It is concluded from the empirical and numerical results that pillar strength deterioration is influenced by an increase in the stope inclination. Furthermore, the inclination introduces a horizontal stress component which increases the pressure acting on a pillar. It is also ascertained that the stress concentration and yielding are more extensive on the acute side of the pillars. Therefore, the appropriate support system requires coupling the 6-set timber props (propsetters) structure with the wedged head and floorboards installed at an offset distance from the mined-out pillars.