Demand for heirloom tomatoes (Solanum lycopersicum L.) and organically grown produce is increasing. The objective of this research was to compare heirloom tomato production in conventional (CS) and organic-transitional (OS) production systems. Heirloom cultivars Arkansas Traveler–the original, Cherokee Purple, Kentucky Beefsteak, Manulucie, and Persimmon Orange were grown in 2007 and 2008 on a raised bed, microirrigated, black plastic mulch culture in a split-plot design with production system as the main plot. Inorganic fertilizer at 160N–13P–50K kg·ha−1 [NH4NO3, Ca(H2PO4)2, KCl] or poultry litter (PL) at 5600 kg·ha−1 was applied in March and soil-incorporated. Transplanting occurred on 12 Apr. 2007 and 22 Apr. 2008. PL supplied 194N–133P–183K and 145N–83P–171K kg·ha−1 potential in 2007 and 2008, respectively. Overall, there were no system effects on total marketable fruit weight, marketable fruit numbers, average fruit weights, total cull weights, or percent marketable yields. Marketable yields averaged across systems ranged from 8,457 to 13,550 kg·ha−1 in 2007 and 1,224 to 5,974 kg·ha−1 in 2008. Weather-delayed transplanting followed by wet and cloudy weather in April and May and greater incidence of tomato spotted wilt virus (TSWV) were suspected for lower yields in 2008. Petiole sap nitrate-N of whole plot treatments were considered within sufficiency levels for both systems when checked at pre- and early harvest. Soil pH of the CS dropped from 7.2 to 5.6 after two seasons but did not change in the OS. Organic production of heirloom tomatoes using PL yielded equivalently to conventional culture for 2 years after transition from conventional management.