Developmental Dyslexia (DD) is a learning disorder characterized by specific difficulties in learning to read accurately and fluently, which has been generally explained in terms of phonological deficits. Recent research has shown that individuals with DD experience timing difficulties in the domains of language, music perception and motor control, probably due to impaired rhythmic perception, suggesting that timing deficit might be a key underlying factor to explain such a variety of difficulties. The present work presents two experiments aimed at assessing the anticipatory ability on a given rhythm of 9-year old Italian children and Italian adults with and without DD. Both adults and children with DD displayed a greater timing error and were more variable than controls in high predictable stimuli. No difference between participants with and without DD was found in the control condition, in which the uncertain timing of the beat did not permit the extraction of regularities. These results suggest that both children and adults with DD are unable to exploit temporal regularities to efficiently anticipate the next sensory event whereas control participants easily are. By showing that the anticipatory timing system of individuals with Developmental Dyslexia appears affected, this study adds another piece of evidence to the multifaceted reality of Developmental Dyslexia.