Handwriting and spelling problems are often associated in dyslexia. However, the nature of their association is still unclear, and most of the existing research in this area is on deep orthographies (mainly English). The extent to which findings are applicable across languages is uncertain. This article examines the effects of script (manuscript/cursive) and orthographic complexity (complex/simple spellings) on the word dictation and word-copying performance of a group of 24 Italian children with dyslexia and handwriting difficulties (DH group, aged 8–10). Their performance was compared with that of a chronologically age–matched group (CA) and a group of younger children matched to the DH group for their handwriting skills (HA: handwriting age group). Children performed two classical handwriting tasks: the alphabet task and a sentence-copy task, and dictation and copy tasks of orthographically complex words and orthographically simple words. Copying was performed in manuscript and cursive. The results show that although the DH group shows a significant deficit in graphomotor processes, orthographic complexity more than the visual-motor characteristics of the task (i.e., script) affects their performance in handwriting. An advantage for cursive script in DH children, but not in the other two groups, emerges from the study.