Mamyshev oscillators (MOs), a new type of femtosecond fiber laser, can produce not only high-performance stationary dissipative solitons (SDSs), but also exhibit chaotic dynamics. Since chaotic behavior may lead to dramatic degradation of the performance, it is particularly important to investigate chaotic dynamics in MOs. Here, using numerical simulation and experimental research methods, we systematically investigate different routes from SDSs to chaos in an MO. Specifically, by simply increasing the gain saturation energy under different polarization states, we obtained different routes from SDSs to chaos, including via a cascade of period-doubling bifurcations (CPDB), via a quasi-cascade of period-doubling bifurcations, and via a double CPDB. In addition, the evolution from dissipative soliton molecules to chaos via CPDB was also observed by increasing the gain saturation energy with a small filter wavelength separation. This finding shows that the evolution from SDSs to chaos is a generic property of laser systems and can appear in various pulse patterns such as single pulse, dissipative soliton molecules, and harmonic mode-locking pulses, which may be beneficial for better understanding chaotic dynamics in MOs.