Cytomegalovirus (CMV) congenital infection and toxoplasmosis share comparable clinical manifestations. The long-term effects of both infections can be lessened with prompt diagnosis and treatment. Although rare, coinfections have been documented. Due to scan abnormalities detected at 31 weeks of pregnancy, dichorionic diamniotic twins born at 35 weeks of gestation were evaluated for congenital infections. The antenatal examinations were held up because of the late booking, and the antenatal examinations of the mother were held up. Both were tested for Toxoplasma gondii infection after they were born with contrasting symptoms. While the 2nd twin’s diagnosis was straightforward, it was more problematic for the 1st twin, who showed a weak positive polymerase chain reaction and inconclusive serology. The discovery further complicated the clinical picture that Twin 1 had congenital CMV. With the long-term effects of toxoplasmosis and the need for serology at 12 months of age for a clear diagnosis, both twins were given therapy early on for congenital toxoplasmosis. As with twin 2, congenital CMV in twin 1 was diagnosed and treated. Congenital toxoplasmosis can be difficult to diagnose since serological studies in newborns have their limits. However, starting therapy early in suspected cases may be required because of the risk of infectious sequelae. Although congenital toxoplasmosis and cytomegalovirus (CMV) have been linked to discordant presentations in twins, coinfection has seldom been observed without immunosuppression. The twin of an infected newborn should be treated with a high level of suspicion because of the likelihood of secondary illnesses. Obtaining an accurate diagnosis and effective treatment requires input from multiple fields of expertise.