Given the potential environmental and economic sustainability consequences of cover crop adoption, N fertilizer application, and residue management, this study focuses on the yield and financial effects of these on processing tomato production in Ontario, Canada. The study employs financial modeling using field data from a long-term cover crop experiment (oat, cereal rye, radish, and a radish-rye mixture) from 2010 to 2020. Averaged over six experimental years, compared to no cover (87 Mg ha−1) radish (99.6 Mg ha−1) and radish-rye mix (95.2 Mg ha−1) cover crops produce statistically significantly higher tomato yields as isolated practices, increasing farm net returns by $1120 ha−1 and $604 ha−1, respectively. When combined with N application, rye application additionally results in tomato yields statistically significantly higher than the base practice of no cover crop, zero N application and retained residue. Oat cover does not appear to have a statistically significant effect on tomato yields in this dataset. The application of N fertilizer results in statistically significantly higher tomato yield, increasing net returns by $882 ha−1, while residue management does not.