We investigated the association of infants' sleep and awake positioning with motor milestone acquisition as measured by the Alberta Infant Motor Scale (AIMS). Participants were 30 very‐low‐birthweight (VLBW) infants with preterm white matter disease (PTWMD; 21 males, nine females; mean birthweight [BW] 1129g [SD 338]; mean gestational age [GA] 28wks [SD 2.44]); 21 VLBW infants without preterm WMD (PT; 13 males, eight females; mean BW 1107g [SD 370]; mean GA 28.05wks [SD 2.21]); and 17 term infants (Term; seven males, 10 females; mean BW 3565g [SD 382]; mean GA 40wks [SD 1.31]). Testing occurred at 1, 5, and 9 months of age (corrected for prematurity). Preferred positions during sleeping, playing, and feeding were obtained through parent interview. These positions and group were the independent variables. Prone sleeping was significantly and positively associated with motor development at all ages (1mo: p=0.005; 5mo: p=0.011; 9mo: p=0.040). At 5 months, prone sleeping and playing were significantly and positively associated with AIMS scores (prone sleeping, p=0.016; prone playing, p=0.047). However, group was negatively associated with preterm white matter disease, with the PTWMD group having significantly lower AIMS scores than the Term group (p=0.029). At 9 months, sitting playing and group membership were significantly associated with AIMS scores (sitting playing, p=0.005; group, p=0.012). Prone positioning should be encouraged for awake time, particularly for infants with preterm white matter disease.