In their first 150 days of lactation, nine Ragusana jennets were investigated at the ‘Istituto Sperimentale Zootecnico per la Sicilia’ (ISZS) in Palermo, to study the effects of different milking typologies on milk production. The jennets were kept in a paddock and were fed hay ad libitum and concentrate (3.5 kg jennet/day). From post-foaling day 21, every 3 weeks individual milk amounts were recorded, and individual milk samples were collected and analyzed for the main qualitative parameters. The compared theses were: two daily milking times with 6- and 3-h intervals; and two, three and eight daily milking times with 3-h interval. The jennets were manually milked. The foals were separated from the jennets at 0800 h, and after the last milking the foals were housed with the jennets. During the day with eight milkings, the milk yield from the jennets was fed to their respective foals, through bottles. The 6-h milking interval produced more milk (+19%) per session than the 3-h interval (P ⩽ 0.01). The fat content per session, with the eight-time milking frequency (P ⩽ 0.001), was greater than the others. For each milking typology, the lactation stage had a similar effect on almost all the considered variables. When observing the eight-milking times, the fat content (%) increased from 1100 to 0500 h (P ⩽ 0.001). The milk yield and the fat percentage produced by two-, three- and eight-milking times were positively correlated.