Despite a dramatic increase of single parenthood during the past decades, parent-child transmission of attachment has almost always been examined in intact families. A first objective of the current study was to examine child attachment in the context of single parenthood, both maternal and paternal. A second objective was to investigate intergenerational transmission of attachment in single parent-child dyads, compared with that observed in two-parent families. The samples consisted of 50 married couples and 43 single parents (22 mothers and 21 fathers), along with their 3- to 6-year-old children. Parental and child attachment representations were measured, respectively, with the Adult Attachment Interview and the Attachment Story Completion Task. Findings suggested that single parenthood per se was not linked to more insecure or disorganized child attachment representations. However, when the father was the sole caregiver, children exhibited more disorganized representations. Different patterns of mother-child associations were found according to family structure: associations were significant among married families but not among single-mother families. Results also replicated those of previous studies in finding a nonsignificant father-child association in two-parent families and a significant one in single-father families, specifically with respect to hyperactivation. Further research is needed to clarify whether the differences found are attributable to different circumstances leading to single parenthood for men and women, or to parental gender itself.