Strong mine pressure often emerges when the working face of the lower coal seam in a closely spaced coal seam system passes through the remaining coal pillar in the overlying goaf. This study investigates the law of overburden movement and the manifestation of mine pressure during mining under the remaining coal pillar. A physical model measuring 2.5 × 0.2 × 1.503 m is constructed. Fiber Bragg grating sensing technology (FBG) and Brillouin optical time domain analysis technology (BOTDA) are employed in the physical model experiment to monitor the internal strain of the overlying rock as the working face advances. This study determines the laws of overlying rock fracture and working face pressure while mining coal seams beneath the remaining coal pillar. It analyzes the relationship between the pressure at the working face and the strain characteristics of the horizontally distributed optical fiber. A fiber grating characterization method is established for the stress evolution law of overlying rock while passing the remaining coal pillar. The experimental results indicated that the fracture angle of overlying rock gradually decreases during the mining stage through and after the coal pillar. In the mining stage through the coal pillar, the cycle pressure step distance of the working face is reduced by 33.3% compared to the stage after mining through the coal pillar. Initially, the strain pattern of the horizontal optical fiber is unimodal when pressure is first applied to the working face, and it transitions from unimodal to bimodal during periodic pressure. The peak value of fiber Bragg grating compressive strain and the range of influence of advanced support pressure are 3.6 times and 4.8 times, respectively, before passing through the remaining coal pillar. Finally, the accuracy of the FBG characterization method is verified by comparing it to the monitoring curve of the coal seam floor pressure sensor. The research results contribute to applying fiber optic sensing technology in mining physical model experiments.