Inadequate winter chill causes poor budbreak in blackberry ( Rubus L. subgenus Rubus Watson), limiting the commercial production in the subtropics. In ‘Natchez’ blackberry, our previous study found that, under inadequate chilling conditions, urea and lime sulfur (LS) applied as defoliants before chill accumulation advanced budbreak but did not improve final budbreak. In this study, we applied the two defoliants at the end of chill accumulation and examined their effectiveness in breaking dormancy, with a hypothesis that it can be enhanced with increased exposure to chilling. Field experiments were conducted over two growing seasons under subtropical climatic conditions. ‘Natchez’ blackberry was sprayed with urea or LS at 10%. Both defoliants were effective in both advancing and maximizing budbreak. Final budbreak reached 42.6% to 76.8% in the defoliant treatments, compared with 27.1% to 31.6% in the control. Advanced budbreak by defoliants increased early season yield by 35% to 88%. Although not statistically significant, defoliants increased total-season yield by 19% to 56%, compared with the control. Phytohormone profiling revealed no changes in abscisic acid and gibberellic acid 4, but increasing trends in jasmonic acid and indole-3-acetic acid (IAA) during budbreak. The LS treatment increased IAA accumulation by up to 377% compared with the control. These results suggest that urea and LS are highly effective dormancy-breaking agents for blackberry when applied after winter chill accumulation. These defoliants could be an important adaptation tool for subtropical blackberry production. Furthermore, increased IAA accumulation appears to be, at least in part, the mode of action for LS-induced budbreak.