Chronic lymphocytic leukaemia (CLL) is the most common leukaemia in the Western world. Despite this fact, its coexistence with pregnancy is extremely rare, with few cases reported in the literature. Given the rarity of this event, it is difficult to conduct large prospective trials to evaluate diagnostic, management, and outcome aspects. The existing evidence is limited to the few published cases and scarce data from reviews on haematological malignancies and pregnancy. Here, we report a case of a 36-year-old patient who had already finished treatment for CLL and was under surveillance when she got pregnant. We describe the evolution of the pregnancy and of the disease's behaviour as well as the oncological and obstetrical management. Being an indolent disease, CLL during pregnancy can be usually followed up without treatment, but infectious and autoimmune complications might have a significant impact on the pregnancy outcome. Therefore, pregnancy must be closely monitored in specialised centres.