Watermelons account for 7% of the world’s fruit vegetable production. In the European market, Spain contributes around 35% of total watermelon supply, with the majority grown in greenhouses in Almería, Southern Spain. This study presents experimental results from the first agrivoltaic watermelon trial conducted in a raspa-y-amagado greenhouse during the 2024 growing season in Almería, Spain. Watermelons were cultivated under two shading treatments with 30% and 50% of the roof area covered with PV modules and compared against an unshaded control group. Throughout the experiment, temperature values in the 30% and 50% zones were 2.2 °C and 4.3 °C lower than in the control zone, respectively. The unshaded control zone and the 30% shading treatment maintained DLI conditions within the optimal range between 21 mol m⁻² d⁻¹ and 32 mol m⁻² d⁻¹ for most of the crop cycle, while the 50% shading zone remained largely above the minimum threshold of 15 mol m⁻² d⁻¹ required for adequate crop growth. No statistically significant differences were observed in fruit weight, rind width, fruit firmness, or soluble solids content at harvest. In addition, the experimentally measured irradiance data from this study were compared with simulations from a previously established irradiance model. The model was applied to the raspa-y-amagado greenhouse, and the experimental data were used to perform a long-term comparison between simulated and measured irradiance for 265 days of data. The irradiance model accurately reproduced shading effects from both the PV modules and greenhouse structure, achieving nRMSE values of 0.09, 0.18, and 0.27 for the control, 30% shading, and 50% shading zones, respectively.