Despite an impressive growth of Ghana's economy over the decades, it has been branded as 'jobless growth' manifested in growing unemployment among the youth. This growing unemployment rate is gender biased against women, with the United Nations expecting this to worsen globally over time. This study examines the determinants of gender-based participation of the youth in income generating enterprises in cocoa growing areas in Ghana, using a sample of 4,702 participants of the Next Generation Cocoa Youth Program (MASO) initiative. This data were obtained by Solidaridad West Africa. The sample was obtained through the Propensity Score Matching (PSM) technique to compare the characteristics of the male and female groups and remove missing observations. The multinomial regression model supported with descriptive analysis were employed for the estimation. It was found that most of those who participated (63%) in the training program were engaged in an income generating activity. Youth engagement in cocoa (9%) as compared with non-cocoa (28%) and joint enterprise (26%) is very low. Given the same level of exposure (MASO), women are more likely to be unemployed, less likely to engage in cocoa production and more likely to be engaged in non-cocoa enterprises. All non-cocoa business enterprises are dominated by men except petty trading and agro processing. Age, marital status, education, savings, additional training, migrant status and gender, influenced engagements in the various categories of enterprises. The study recommends rolling out other policies that can address challenges of women engagement in cocoa farming in addition to the training program. Policies towards encouraging savings among the youth is recommended to aid in startup businesses, which may be supported by low interest loans. Attention should be given to the non-cocoa sector in terms of employment as people are either losing interest in cocoa farming or diversifying their incomes to non-cocoa businesses.