Joints and fissures with similar orientation or characteristics are common in natural rocks; the inclination and density of the fissures affect the mechanical properties and failure mechanism of the rock mass. However, the strength, crack coalescence pattern, and failure mode of rock specimens containing multi-fissures have not been studied comprehensively. In this paper, combining similar material testing and discrete element numerical method (PFC2D), the peak strength and failure characteristics of rock-like materials with multi-fissures are explored. Rock-like specimens were made of cement and sand and pre-existing fissures created by inserting steel shims into cement mortar paste and removing them during curing. The peak strength of multi-fissure specimens depends on the fissure angle α (which is measured counterclockwise from horizontal) and fissure number (Nf). Under uniaxial compressional loading, the peak strength increased with increasing α. The material strength was lowest for α = 25°, and highest for α = 90°. The influence of Nf on the peak strength depended on α. For α = 25° and 45°, Nf had a strong effect on the peak strength, while for higher α values, especially for the 90° sample, there were no obvious changes in peak strength with different Nf. Under uniaxial compression, the coalescence modes between the fissures can be classified into three categories: S-mode, T-mode, and M-mode. Moreover, the failure mode can be classified into four categories: mixed failure, shear failure, stepped path failure, and intact failure. The failure mode of the specimen depends on α and Nf. The peak strength and failure modes in the numerically simulated and experimental results are in good agreement.