Background: Rural medical workforce shortage contributes to health disadvantage experienced by rural communities worldwide. This study aimed to determine the regional results of an Australian Government sponsored national program to enhance the Australian rural medical workforce by recruiting rural background students and establishing rural clinical schools (RCS). In particular, we wished to determine predictors of graduates’ longer-term rural practice and whether the predictors differ between general practitioners (GPs) and specialists. Methods: A cross-sectional cohort study, conducted in 2012, of 729 medical graduates of The University of Queensland 2002–2011. The outcome of interest was primary place of graduates’ practice categorised as rural for at least 50% of time since graduation (‘Longer-term Rural Practice’, LTRP) among GPs and medical specialists. The main exposures were rural background (RB) or metropolitan background (MB), and attendance at a metropolitan clinical school (MCS) or the Rural Clinical School for one year (RCS-1) or two years (RCS-2). Results: Independent predictors of LTRP (odds ratio [95% confidence interval]) were RB (2.10 [1.37–3.20]), RCS-1 (2.85 [1.77–4.58]), RCS-2 (5.38 [3.15–9.20]), GP (3.40 [2.13–5.43]), and bonded scholarship (2.11 [1.19–3.76]). Compared to being single, having a metropolitan background partner was a negative predictor (0.34 [0.21–0.57]). The effects of RB and RCS were additive—compared to MB and MCS (Reference group): RB and RCS-1 (6.58 [3.32–13.04]), RB and RCS-2 (10.36[4.89–21.93]). Although specialists were less likely than GPs to be in LTRP, the pattern of the effects of rural exposures was similar, although some significant differences in the effects of the duration of RCS attendance, bonded scholarships and partner’s background were apparent. Conclusions: Among both specialists and GPs, rural background and rural clinical school attendance are independent, duration-dependent, and additive, predictors of longer-term rural practice. Metropolitan-based medical schools can enhance both specialist and GP rural medical workforce by enrolling rural background medical students and providing them with long-term rural undergraduate clinical training. Policy settings to achieve optimum rural workforce outcomes may differ between specialists and GPs.