Two end-functionalized solution polymerized styrene-butadiene rubber was synthesized through anionic polymerization for using in formulation of well-dispersed silica compounds with study the wear behavior of the vulcanizates. Polymerization and functionalization were analyzed and confirmed via FT-IR, GPC, and NMR analyses. Novel functionalization, using an amine-containing agent, improved the distribution of silica. With the fine dispersion of silica, the wear rate dropped; the correlations between vulcanizate abrasion resistance, hardness, tear strength, glass transition temperature, and the SEM micrographs of the worn surface were studied. The abrasive stick-slip process was the primary wear mechanism and pattern spacing was the least for amino-modified vulcanizates. Lower reinforcement caused deep grooves, scratches, and pits in the non-modified sample. The amino-functionalized samples had desirable SEM characteristics, low hardness, more dispersed silica with fewer agglomerates and higher tear strength, confirming the higher interaction of silica particles and rubber chains.