The geometry and orientation of cavities in a rock mass has a significant influence on the failure mechanism and fracture propagation. The theoretical study of these behaviors is of great importance to enable fundamental understanding of unstable failure in rock mechanics. A very limited number of experimental studies have been conducted for sandstone specimens containing oval cavities. Sensitive parameters include the short axis (b) to long axis (a) ratio. Here, we enhance the present understanding of crack coalescence behavior around an oval cavity by applying uniaxial compression tests to sandstone cores containing manually inserted single oval cavity, combined with photographic and acoustic emission monitoring. The b:a ratio was varied from 1/4 to 1/1, thus the cross-sectional cavity shape evolved from oval to a fully circular opening. The experimental results showed that the stress–strain curves of specimens containing cavities exhibited multiple stress reductions prior to peak strength, which led to a sudden increase in the accumulated AE count-rate. As the b:a ratio was increased, the uniaxial compressive strength, crack initiation stress and peak strain of cavity specimens all decreased linearly. Tensile fractures, shear fractures, and compound shear-tensile fractures were all observed to emanate from the cavities. Compared to the intact specimen, the failure mode of cavity specimens comprised a mixture of tensile and shear cracks, emanating from the tips (or surfaces) of the oval cavity. For specimen with a cavity angle of 45°, when the b:a ratio was below 1/2, no tensile crack from the surface of short axis was initiated, whereas tensile crack was observed clearly after b:a = 1/2. This study not only increases our understanding of mechanical failure behavior in fractured rock, but also enhances our knowledge of underground tunneling or roadway stability.