This study tested the hypotheses that machine milked dairy sheep have a high prevalence of teat-end hyperkeratosis (TEH), which contributes to udder health problems. A random sample of 1360 milking ewes from 28 dairy sheep farms was monitored. Milking procedures, milking parlour characteristics and maintenance were recorded during a designated on farm audit; records were obtained through observations and interviews with farmers. Number of ewes/milker, ewes/milking unit and milkings/milking unit were calculated. Vacuum level, pulsation rate and ratio were measured. Four combinations of vacuum level and pulsation rate were defined; <40 kPa and <150 cycles/min (VP1), <40 kPa and ≥150 cycles/min (VP2), ≥40 kPa and <150 cycles/min (VP3), ≥40 kPa and ≥150 cycles/min (VP4). California Mastitis Test (CMT; scores 0–4) was done on all ewes. Then the udder of each ewe was assessed for TEH (scores 1–4) and ewes were assigned into three groups according to TEH severity (no or mild, medium and severe TEH). Severe TEH (scores 3 and 4) prevalence at teat-level was ca. 13%. TEH severity was associated with the combination of vacuum level and pulsation rate; ewes milked with VP4 combination were more likely to have a one-level increase on TEH severity compared to ewes milked with VP2 and VP3 combinations. More ewes/milker and less ewes/milking unit increased the likelihood of a one-level increase on TEH severity. Finally, ewes with severe TEH were more likely to have a one-level increase on CMT score. Therefore, our hypotheses that TEH is prevalent in dairy ewes and contributes to udder health problems were confirmed. Additionally, farmers can reduce TEH prevalence by optimising the way they milk and their milking parlour.