The fracturing behaviors of serial coal pillars is significant for understanding their failure mechanism. To reveal this, the bearing stress, acoustic emission, electrical resistivity, local strain, force chain distribution, and cracks evolution of serial coal pillars under uniaxial compression were evaluated by experiment and numerical simulation. The results show that four bearing stages are observed during the fracturing process (i.e., nonlinear growth, linear growth, yielding growth, and weakening stages). The acoustic emission features, electrical resistivity responses, strain develops, force chain distributions, cracks evolutions, and local displacement are highly consistent to illustrate the fracturing behaviors. System fracturing of serial coal pillar specimens is appeared along with the collapse of lower uniaxial compressive strength coal pillar specimen. The limit bearing capacity of serial coal pillar specimens is almost equal to the strength of lower uniaxial compressive strength coal pillar specimen. The unbalanced deformation characteristics of serial coal pillar specimens are presented due to the strength differences. The evolution of the key deformation element is the rooted reason for the overall fracturing mechanism of serial coal pillar specimens. For serial coal pillar specimens with different strengths, the critical condition of system fracturing is that the sum of secant modulus of upper and bottom coal pillars is zero, which is expected to predict the system fracturing of serial pillars in the underground coal mining.