The availability of irrigation water of good quality is decreasing due to soil salinization and the deterioration of aquifers. Moreover, ongoing climate change severely affects crop production and necessitates the intensification of cropping systems in order to ensure food security at a global scale. For this purpose, the aim of the present study was to evaluate the mitigating effects of two natural biostimulants on Diplotaxis tenuifolia L. plants cultivated at different salinity levels (EC of 0 dS m−1, 2 dS m−1, 4 dS m−1, and 6 dS m−1) and harvested at six consecutive cropping cycles. The tested factors showed a varied combinatorial effect on the tested parameters. These findings indicate the importance of considering growing conditions and cropping periods when applying biostimulants in D. tenuifolia plants under salinity stress. Antioxidant activity and bioactive compounds, such as total phenols, carotenoids, and total ascorbic acid, were variably affected by salinity, biostimulant application, and harvesting time, while mineral profile was also affected by the tested factors depending on the combination of factors. Finally, nitrate content showed decreasing trends with increasing salinity, while biostimulant application resulted in the higher accumulation of nitrates compared to the untreated plants. Although biostimulant application seems to alleviate the negative effects of salinity stress, the effect of growing conditions, as indicated by successive crop cycles, is also important for the response of D. tenuifolia plants to saline conditions and biostimulant application.