Leptospirosis in pregnancy is often underdiagnosed and not commonly reported due to its unusual appearance and rarity. It looks like HELLP syndrome, obstetric cholestasis, viral hepatitis & pregnancy-related acute fatty liver. Miscarriages in the first trimester, stillbirths, and neonatal leptospirosis are serious complications that necessitate a high degree of concern, heightened sensitivity, and prompt diagnosis and treatment. We have one such incidence of leptospirosis in a COVID-19 positive pregnant female. A 21-year-old Primigravida with a predisposition of serious anaemia & thrombocytopenia, presented with fever, haematemesis, malena and sore throat at 38 weeks and 2 days gestation, during the COVID-19 pandemic. She had pallor, oedema, and haematuria on catheterization, rest all investigations were within normal limits. Proteinuria, haemolysis, low platelets, and elevated bilirubin were discovered during the investigation. Due to the lack of hypertension and elevated transaminases, the working diagnosis was atypical haemolysis, low platelets (HELLP) syndrome. The patient was tested for COVID-19 RT-PCR, came out to be positive and the fever spikes continued, leading to further investigations for Dengue, Malaria, Scrub Typhus, and Leptospirosis due to the ongoing Covid-19 pandemic. After the EIA (Enzyme Immunoassay) IgM antibody (confirmatory for Leptospirosis) tested positive for Leptospirosis, the decision to start Doxycycline was made. Meanwhile, the patient's CTG (Cardio tocograph) revealed signs of foetal distress, and a decision for an emergency LSCS was taken (Lower Segment Caesarean Section). The histology of the placenta after the section revealed normal findings. Doxycycline was initiated with a neonatal feeding regimen that was acceptable. On day two of life, the newborn had no indications of inherited leptospirosis and was removed from Neonatal Intensive Care. Within one week, the patient's symptoms had disappeared, and her biochemistry had went back to normal within 2 weeks.