This study examines the behavior of anisotropically consolidated granular assemblies under undrained cyclic true triaxial loading paths. To achieve this, the Discrete Element Method (DEM) is conjugated with the Coupled Fluid Method (CFM) to account for fluid-solid interaction in undrained conditions. The examined loading paths include two phases: anisotropic consolidation and undrained cyclic true triaxial loading. During consolidation, samples are sheared at various Lode angles to reach a spectrum of initial static shear stress levels. In the second stage, undrained cyclic loading is applied with constant shear stress amplitudes at various Lode angle values. The results indicated that the monotonic and cyclic Lode angle, initial static shear stress, and amplitude of deviatoric stress have pronounced effects on the secant shear modulus degradation and the rate of excess pore water pressure generation of granular assemblies. In tandem with macro-scale observations, the evolution of the microstructure within assemblies is analyzed using the coordination number, redundancy index, inter-particle contact fabric tensor, and particle orientation fabric tensor. The micro-scale findings confirm that the anisotropy induced by changes in the loading direction significantly impacts the shear strength of the assemblies. Additionally, the fabric of assemblies aligns along the preferential direction corresponding to the major principal stress, influencing the dilative response.