Difficulties in mathematics have been described in very preterm children, but their origins are not well understood and may differ from other populations with specific learning disability. Very preterm children, children with learning disability, and typically developing children were compared in mathematics skills, using standardized tools, experimental tasks, and eye-tracker measures. We assessed symbolic and nonsymbolic magnitude comparisons, number knowledge, calculation, as well as cognitive skills of 103 Italian-speaking fourth and fifth graders. Compared to typically developing peers, very preterm children showed delays in number knowledge, slower reaction times in nonsymbolic magnitude comparisons, and an atypical gaze exploration characterized by more and shorter fixations that lacked a target preference. The profile of mathematics skills of very preterm children appeared different from that of children with learning disability. Although both populations showed mainly preserved cognitive skills and slower reaction times in nonsymbolic magnitude comparisons, children with specific learning disability showed more severe impairments in calculation and were slower in symbolic magnitude comparisons, compared to very preterm children. Including eye-tracking measures in preterm follow-up programs and planning tailored interventions are recommended.