The evolution of photosynthetic reaction centers (RCs) from anoxygenic bacteria to higher-order oxygenic cynobacteria and plants highlights a remarkable journey of structural and functional diversification as an adaptation to environmental conditions. The role of chirality in these centers is important, influencing the arrangement and function of key molecules involved in photosynthesis. Investigating the role of chirality may provide a deeper understanding of photosynthesis and the evolutionary history of life on Earth. In this study, we explore chirality-related energy transfer in two evolutionarily distinct RCs: one from the anoxygenic purple sulfur bacterium Thermochromatium tepidum (BRC) and the other from the oxygenic cyanobacterium Thermosynechococcus vulcanus (PSII RC), utilizing two-dimensional electronic spectroscopy (2DES). By employing circularly polarized laser pulses, we can extract transient chiral dynamics within these RCs, offering a detailed view of their chiral contribution to energy transfer processes. We also compute traditional 2DES and compare these results with spectra related to circular dichroism. Our findings indicate that two-dimensional circular dichroism spectroscopy effectively reveals chiral dynamics, emphasizing the structural symmetries of pigments and their interactions with associated proteins. Despite having similar pigment-protein architectures, the BRC and PSII RC exhibit significantly different chiral dynamics on an ultrafast time scale. In the BRC, the complex contributions of pigments such as BChM, BPhL, BCh, and PM to key excitonic states lead to more pronounced chiral features and dynamic behavior. In contrast, the PSII RC, although significantly influenced by ChlD1 and ChlD2, shows less complex chiral effects and more subdued chiral dynamics. Notably, the PSII RC demonstrates a faster decay of coherence to localized excitonic populations compared to the BRC, which may represent an adaptive mechanism to minimize oxidative stress in oxygenic photosystems. By examining and comparing the chiral excitonic interactions and dynamics of BRC and PSII RC, this study offers valuable insights into the mechanisms of photosynthetic complexes. These findings could contribute to understanding how the functional optimization of photosynthetic proteins in ultrafast time scales is linked to biological evolution.