An extensive body of theoretical work has advocated the use of multiple human wellbeing indicators to assess the outcomes of agricultural investments in Sub-Sahara Africa (SSA). However, few studies have actually achieved it. This study investigates the human wellbeing outcomes of involvement in industrial crop production in Ghana by comparing the levels of different objective and subjective wellbeing measures for groups involved in industrial crop production as plantation workers and smallholders, and groups not involved (i.e. control groups). We use household income, adult consumption and the multidimensional poverty index (MPI) as indicators of objective wellbeing. We measure subjective wellbeing through self-reported levels of satisfaction with life, worthwhileness, happiness and anxiousness. Propensity Score Matching (PSM) analysis is used to assess whether involvement in industrial crop production increases household income and consumption. Overall, for most indicators of objective wellbeing industrial crop outgrowers, smallholders and independent smallholders are better off compared to other groups in their respective sites (in terms of mean scores), but involvement does not necessarily brings human wellbeing benefits (PSM analysis). On the other hand plantation workers are either worse off or have similar level of objective human wellbeing with control groups in their respective sites (in terms of mean scores), but involvement sometimes brings human wellbeing benefits (PSM analysis). However, workers tend to benefit from access to plantation infrastructure, which has a positive effect to their multi-dimensional poverty. In most cases the objective wellbeing measures do not correlate well with self-reported levels of subjective wellbeing. It is important to combine such indicators when evaluating the human wellbeing outcomes of agricultural investments in order to obtain a more comprehensive outlook of whether industrial crop production can become a valuable rural development strategy in SSA.