Insecticides and fungicides present potential threats to non-target crops, yet our comprehension of their combined phytotoxicity to plants is limited. Silicon (Si) has been acknowledged for its ability to induce crop tolerance to xenobiotic stresses. However, the specific role of Si in alleviating the cypermethrin (CYP) and hymexazol (HML) combined stress has not been thoroughly explored. This study aims to assess the effectiveness of Si in alleviating phytotoxic effects and elucidating the associated mechanisms of CYP and/or HML in tomato seedlings. The findings demonstrated that, compared to exposure to CYP or HML alone, the simultaneous exposure of CYP and HML significantly impeded seedling growth, resulting in more pronounced phytotoxic effects in tomato seedlings. Additionally, CYP and/or HML exposures diminished the content of photosynthetic pigments and induced oxidative stress in tomato seedlings. Pesticide exposure heightened the activity of both antioxidant and detoxification enzymes, increased proline and phenolic accumulation, and reduced thiols and ascorbate content in tomato seedlings. Applying Si (1 mM) to CYP- and/or HML-stressed seedlings alleviated pigment inhibition and oxidative damage by enhancing the activity of the pesticide metabolism system and secondary metabolism enzymes. Furthermore, Si stimulated the phenylpropanoid pathway by boosting phenylalanine ammonia-lyase activity, as confirmed by the increased total phenolic content. Interestingly, the application of Si enhanced the thiols profile, emphasizing its crucial role in pesticide detoxification in plants. In conclusion, these results suggest that externally applying Si significantly alleviates the physio-biochemical level in tomato seedlings exposed to a combination of pesticides, introducing innovative strategies for fostering a sustainable agroecosystem.