Silica-filled styrene butadiene rubber (SBR)/butadiene rubber (BR) compounds plasticized with mineral oils are mainly used to produce green tire treads. Previous works have demonstrated that the partial replacement of naphthenic oil (ONAF) by bio-based oils can provide processing and performance improvements for rubber compounds, along with environmental benefits. In this study, two modified soybean oils (esterified, OEST or esterified and epoxidized, OEPX) were investigated with the aim of evaluating the complete replacement of ONAF and determining whether the chemical properties of the oils affect the performance of silica-filled E-SBR/BR compounds, using the compound with ONAF as a reference. The physical properties, curing characteristics, morphology, and dynamic mechanical behavior were evaluated. The use of the modified soybean oils decreased the optimal cure time while increasing the crosslink density and the abrasive wear resistance. Further, the compounds with both modified soybean oils showed a good balance of mechanical properties. The modified soybean oils decreased the glass transition temperature of the rubber compounds, thus acting as true plasticizers. At 0°C, the tan δ value of E-SBR/BR/OEPX increased relative to that of E-SBR/BR/ONAF, whereas at 60°C, the values of the compounds with both modified soybean oils showed slight increases. The tan δ values reveal that compared with E-SBR/BR/ONAF, E-SBR/BR/OEPX has better wet grip and a similar rolling resistance, whereas E-SBR/BR/OEST has a higher rolling resistance. Thus, both modified soybean oils can fully replace ONAF and appear to be extremely attractive plasticizers for use in silica-filled E-SBR/BR compounds employed as green tire treads for passenger cars.