Little is known about how HIV impacts directly and indirectly on receiving, or particularly succeeding in, education in sub-Saharan Africa. To address this gap, we used multivariable logistic regression to determine the correlation between education outcomes in youth (aged 15–24) (being in the correct grade-for-age, primary school completion and having at least five “O” level passes) and being HIV-positive; having an HIV-positive parent; being a young carer; or being a maternal, paternal or double orphan, in five rounds (1998–2011) of a general population survey from eastern Zimbabwe. The fifth survey round (2009–2011) included data on children aged 6–17, which were analysed for the impacts of the above risk factors on regular attendance in primary and secondary schools and being in the correct grade-for-age. For data pooled over all rounds, being HIV-positive had no association with primary school completion, “O” level passes, or being in the correct grade-for-age in adolescents aged 16–17 years. Additionally, HIV status had no significant association with any education outcomes in children aged 6–17 surveyed in 2009–2011. In 2009–2011, being a young carer was associated with lower attendance in secondary school (69% vs. 85%, AOR: 0.44; p = 0.02), whilst being a maternal (75% vs. 83%, AOR: 0.67; p < 0.01), paternal (76% vs. 83%, AOR: 0.67; p = 0.02) or double (75% vs. 83%, AOR: 0.68; p = 0.02) orphan was associated with decreased odds of being in the correct grade-for-age. All forms of orphanhood also significantly decreased the odds of primary school completion in youths surveyed from 1998 to 2011 (all p < 0.01). We found no evidence that HIV status affects education but further evidence that orphans do experience worse education outcomes than other children. Combination approaches that provide incentives for children to attend school and equip schools with tools to support vulnerable children may be most effective in improving education outcomes and should be developed and evaluated.