Progressive goaf advancement during extraction of coal in Continuous Miner (CM) workings induces significant stress redistribution, deformation, and failure zones within the active mining zone (AMZ). Analysing these effects on underground workings is essential to understand the global stability of mine. Thus, this paper presents combined approaches utilising field investigations and numerical modeling with FLAC3D to examine the effects of real-time progressive goaf advancement in CM workings. The simulation results indicated that induced stresses mounted up at the immediate goaf-adjacent pillars, leading to increased stress concentration at the pillar edges and gradual stress dissipation towards the pillar core. Vertical displacement in the roof intensifies with advancing goaf, with junctions experiencing the highest deformation due to stress concentration and weakening of the immediate roof strata. Further, an attempt was made to identify the caving zone and its angle based on varying geomining effects during extraction. Thus, these findings provide critical insights into the behaviour of underground coal structures under dynamic mining conditions, emphasizing the importance of effective ground control strategies for safer and more efficient coal recovery.