To identify the most suitable combination of two components, viz., sowing window and genotype for minimising disease incidence and maximising yield and quality of tomato, the current study was conducted in Northern Tripura during the autumn–winter season. The overall findings of the trial revealed that the negative impacts of high and frequent occurrences of tomato diseases, including tomato yellow leaf curl virus (TYLCV), bacterial wilt, early and late blight, on the yield and quality characteristics of tomato. Delayed transplanting, particularly on 7th December, significantly increased the intensities of TYCLV, bacterial wilt, early and late blight of 18.69 %, 10.61 %, 5.55 % and 6.45 %, respectively, observed in the Local cultivar. In contrast, transplanting during 7th and 21st October recorded comparatively lower disease pressure and reduced yield loss. Among the genotypes, Arka Abhed, Arka Rakshak and Arka Samrat consistently exhibited superior performance with higher yield (66.25 t ha-1), lower yield loss (1.61 %) and improved quality attributes, including higher lycopene (56.43 mg 100 g-1) and carotenoid (104.00 mg 100 g-1) contents. The interaction between genotype and sowing window significantly influences disease dynamics, indicating that both genetic resistance and optimal planting time play a crucial rule in disease management. From this, it can be inferred that growing tomatoes in these regions during the autumn-winter months would be most fruitful, if carried out between the second and last weeks of October, using varieties such as Arka Abhed, Arka Rakshak and Arka Samrat.