Existing megawatt-scale photovoltaic (PV) power plant producers must understand that simple and low-cost Operation and Maintenance (O&M) practices, even executed by their own personal and supported by a comparison of field data with simulated ones, play a key role in improving the energy outputs of the plant. Based on a currently operating 18 MW PV plant located in an under-developing South-Asia country, we show in this paper that comparing real field data collected with simulated results allows a central vision concerning plant underperformance and valuable indications about the most important predictive maintenances actions for the plant in analysis. Simulations using the globally recognized software PVSyst were first performed to attest to the overall power plant performance. Then, its energy output was predicted using existing ground weather data located at the power plant. Compared with the actual plant’s annual energy output, it was found that it was underperforming by −4.13%, leading to a potential monetary loss of almost 175,000 (EUR)/year. Besides, an analysis of the O&M power plant reports was performed and compared to the best global practices. It was assessed that the tracker systems’ major issues are the forerunner of the most significant PV power plant underperformance. In addition, issues in inverters and combiner boxes were also reported, leading to internal shutdowns. In this case, predictive maintenance and automated plant diagnosis with a bottom-up approach using low-cost data acquisition and processing systems, starting from the strings level, were recommended.