Objective To investigate the structural brain abnormalities and their diagnostic accuracy through qualitative and quantitative analysis in term born and very preterm birth or with very low birthweight (VP/VLBW) adults. Methods: We analyzed 3T MRIs acquired 2011-2013 from 67 adults (27 term born controls, mean age 26.4 years, 8 females; 40 VP/VLBWs, mean age 26.6 years, 16 females). We compared automatic segmentations of white matter, deep grey matter and cortical grey matter, manual corpus callosum measurements and visual ratings of the ventricles and white matter with t-tests, logistic regression and receiver operator characteristic (ROC) curves. Results: Automatic segmentation correctly classified 84% of cases; visual ratings correctly classified 63%. Quantitative volumetry based on automatic segmentation revealed higher ventricular volume, lower posterior corpus callosum and deep grey matter volumes in VP/VLBW subjects compared to controls (P<0.01). Visual rating and manual measurement revealed a thinner corpus callosum in VP/VLBW adults (P=0.04), deformed lateral ventricles (P=0.03) and tendency towards more "dirty" white matter (P=0.06). Automatic/manual measures combined with visual ratings correctly classified 87% of cases. Stepwise logistic regression identified three independent features that correctly classify 81% of cases: ventricular volume, deep grey matter volume and white matter aspect. Conclusion: Enlarged and deformed lateral ventricles, thinner corpus callosum and "dirty" white matter are prevalent in preterm born adults. Their visual evaluation has low diagnostic accuracy. Automatic volume quantification is more accurate but time consuming. It may be useful to ask for prematurity before initiating further diagnostics in subjects with these alterations.