The present study examined whether literacy difficulties in both grades 2 and 3 are associated with social and generalized anxiety within the school environment in grade 5 and if children with different literacy difficulties differ in anxiety levels compared to typically developing children in grade 5 after controlling for inattention. Sixty-nine Greek children with literacy difficulties and fifty-two children with typical literacy development were assessed at the beginning of grade 2 and at the end of grade 3 on standardized literacy measures (reading accuracy, text-reading fluency, reading comprehension, and spelling). In grade 5, teachers were asked to rate their children's social and generalized anxiety levels and inattentive behavior in the school context. Results of one-way ANCOVAs showed that children with literacy difficulties were experiencing more social anxiety than typically developing children. Furthermore, children with both reading and spelling difficulties, but not those with single reading or spelling difficulties, had more social anxiety. These findings suggest that there is a close connection between early literacy difficulties and social anxiety in upper elementary grades and particularly among children with both reading and spelling difficulties. Implications for both teachers and other professionals who support children's socioemotional development will be discussed.