Root dilaceration (DL) has a significant impact on orthodontic treatment. However, its etiology is still debatable. One of the etiologic factors of DL is the dentigerous cyst (DC); therefore, the aim of our case-series clinical study was the association between DL and DCs. This retrospective study is comprised of five clinical cases of DL associated with the presence of DCs of developmental origin. In all of these cases, other dental anomalies (impaction, transposition, supernumerary teeth, and congenitally missing teeth) were found, and accordingly, the association between DL and DCs might be of genetic origin in a dental anomaly pattern.