Syphilis in pregnancy remains an important medical condition due to its consequences. We present two cases of young pregnant women who were diagnosed syphilis during their antenatal visit. The first case was a 29-year-old Malay lady diagnosed with syphilis during the first trimester of pregnancy, while the second case was a 21-year-old Chinese lady diagnosed with syphilis during the third trimester of pregnancy. The diagnosis and management of the syphilis in pregnancy are discussed.