Children with hearing loss (HL) are at risk for a lower educational achievement. This longitudinal study compared the school career of a nationwide Dutch cohort with and without HL based on descriptive data of the governmental authority Statistics Netherlands. From 2008 to 2018, 3,367,129 children, of whom 1,193 used cochlear implants (CIs) and 8,874 used hearing aids (HAs), were attending primary and/or secondary education. Sixty-one percent of children with HL attended mainstream and 31% special primary education. Compared to mainstreamed pupils without HL, mainstreamed pupils with HL achieved lower levels for language and mathematics in primary education but eventually attended comparable types of secondary education. Children with HL attending special primary education attained lower types of secondary education compared to mainstreamed peers with and without HL. These findings suggest that future educational (and as a result professional) attainment of a child with HL depends on the type of primary educational setting.