This research presents both qualitative and quantitative analyses of tool wear during slot milling of Ti-6Al-4V alloy under conventional flood coolant and sustainable dry and minimum quantity lubrication (MQL) machining conditions. The microstructures of the cutting tools near the cutting edges have been analyzed for understanding the effectiveness of tool coating and the influence of tool wear and machining conditions on the tool microstructure. The abrasion wear was measured using maximum flank wear (VBmax) and the length over which the flank wear occurred. The chipping wear was measured using the surface area of the material chipped off from the cutting edge or tool nose. In addition, the correlations between the abrasion and chipping wear with plastic failure were investigated. It was found that the average magnitudes of VBmax and length were lower in MQL machining. The calculations of the surface area of chipped materials indicate comparatively lower chipping wear in MQL machining. Both the abrasion and chipping wear occurred along with plastic failure, indicating correlations among those wear mechanisms. It turned out that the TiAlN-coating was more effective in the reduction of tool wear under dry machining conditions. Delamination wear was observed under flood and MQL conditions, illustrating the effectiveness of coated tools under dry machining conditions. The microstructural analysis of the worn-out uncoated tools indicates plastic deformation and grain refinement underneath the tool wear, whereas this effect is less severe in coated tools. Conclusively, sustainable dry machining with TiAlN-coated tools and MQL machining resulted lesser tool wear, indicating the effectiveness of sustainable machining processes for Ti-6Al-4V alloy.