Life history theory and most empirical studies assume carry-over effects of larval conditions to shape adult fitness through their impact on metamorphic traits (age and mass at metamorphosis). Yet, very few formal tests of this connection across metamorphosis exist, because this entails longitudinal studies from the egg stage and requires measuring fitness in (semi)natural conditions. In a longitudinal one-year common-garden rearing experiment consisting of an outdoor microcosm part for the larval stage and a large outdoor insectary part for the adult stage, we studied the effects of two factors related to time constraints in the larval stage (egg hatching period and urbanisation) on life history traits and lifetime mating success in the males of the damselfly Coenagrion puella. We reared early- and late-hatched larvae from each of three rural and three urban populations from the egg stage throughout their adult life. Key findings were that both the hatching period and urbanisation shaped adult fitness, yet through different pathways. As expected, the more time-constrained late-hatched individuals accelerated their larval life history and this was associated with a lower lifetime mating success. A path analysis revealed this carry-over effect was mediated by the changes in the two metamorphic traits (reduced age and lower mass at emergence). Notably, urban males had a 50% lower lifetime mating success, which was not mediated by age and mass at emergence, and possibly driven by their shorter lifespan. Our results point to long-term carry-over effects of the usually ignored natural variation in egg hatching dates, and further contribute to the limited evidence showing fitness costs of adjusting to an urban lifestyle.