The technology of hybrid breeding in diploid potatoes creates opportunities to design novel and improved cultivation systems based on hybrid true potato seeds. A promising cultivation pathway to produce seed or ware tubers is by transplanting greenhouse-raised seedlings into the field. This study explored the effects of transplanting date and seedling age on tuber yield, using greenhouse-raised seedlings. Field trials with experimental hybrid genotypes were conducted in three consecutive years. In 2017 and 2018, 4- and 6-week-old seedlings were transplanted at four dates: March, April, May and June. In 2019, transplanting dates included April, May and June and seedling age was 5 weeks. In 2018, the March planting experienced severe frost during the initial field period resulting in crop failure. In 2017 and 2019, plants could withstand shorter and less severe frost events. Seedling age did not significantly affect tuber parameters. Transplanting in June resulted in lower marketable yield (> 28 mm) compared with earlier transplanting dates when crops were harvested in September. At full crop senescence, no differences in marketable yield were observed. The optimal transplanting window, taking into account weather-related risks, is approximately between early April and end May. For some genotypes, crop cycle length was observed to be a more important yield-determining factor than transplanting date.