Time of shearing affects many aspects of wool production and sheep health but no study has examined these factors concurrently in a spring-lambing, self-replacing Merino flock in southern Australia. A 5-year field experiment compared wool production in spring-lambing Merino ewes and their progeny shorn at different times and managed under commercial conditions in south-eastern Australia. Groups of 200 adult ewes were shorn in December, March or May, and their progeny were shorn in December or October, March or June, or May or July, respectively. There was no consistent association between time of shearing and the staple strength of wool (P = 0.73). December-shorn ewes produced significantly lighter and finer fleeces (average 19.1 μm, 3.0 kg clean weight) than did March-shorn ewes (19.4 μm, 3.1 kg). Fleeces from ewes shorn in May were of similar weight to those from March-shorn ewes (3.1 kg), but they were of significantly broader diameter (19.7 μm). In young sheep, desirable changes in some wool characteristics for each shearing group were offset by undesirable changes in others. On the basis of median historical (1991–2006) wool prices, shearing ewes in March and their progeny first in June produced the greatest total value of wool over a sheep’s lifetime ($161/head). The wool values per head for other shearing times were as follows: March (weaners)–March (ewes): $158; October–December: $157; December–December: $153; July–May: $151; and May–May: $148. Thus, December and March shearing were appropriate alternatives for maximising wool value produced from a self-replacing Merino flock in south-eastern Australia, whereas May was a less preferable shearing time because it always produced wool of lesser value.