Tomato production faces challenges such as high input costs, pests, diseases, and climate change. Biostimulants like Nurspray®, based on hydroxycinnamic acid oligomers, offer a promising solution. This study evaluated the impact of different application timings of Nurspray® on tomato yield and fruit quality under open-field conditions. Four treatments were tested: T1 (control), T2 (Nurspray® at BBCH 19–51), T3 (Nurspray® at BBCH 19–51–61), and T4 (Nurspray® at BBCH 19–23–51). The results showed significant improvements in root development, canopy cover, and flowering for T3 and T4, with root systems increasing by up to 103% in T4 compared to the control. Fruit yield and quality were enhanced, with a reduction in blossom-end rot (BER) incidence to 0% in T3 and T4, compared to 5% in the control. Additionally, T4 produced the highest dry matter content in fruits. The optimal application strategy was three doses of Nurspray® at BBCH 19–23–51, enhancing both yield and fruit quality. This study highlights the potential of Nurspray® as an organic biostimulant in sustainable tomato farming.