Objective: Colorectal cancer (CRC) during pregnancy is a rare occurrence, with a reported incidence of 0.8 cases per 100,000 pregnancies. Managing CRC during pregnancy poses substantial challenges for clinicians: the diagnosis is often complicated and delayed due to symptom overlap with pregnancy-related manifestations, and medical imaging is constrained by safety concerns for the foetus. Methods: This article presents two cases of advanced CRC diagnosed and managed during pregnancy. Additionally, we conducted a systematic review of the literature to assess diagnostic and prognostic factors involved in CRC in pregnant individuals. The systematic review, with pre-registration and approval through Prospero, involved an extensive search of medical databases (Pubmed, Web of Science, Scopus and Scholar) and statistical analysis using t-test for continuous variables and chi square for dichotomous variables. Results: A total of 1058 studies were identified. After applying exclusion criteria, sixty-six studies were included. Women whose initial symptoms were severe abdominal pain not responsive to common medical treatments and constipation (acute abdomen) had a mean gestational age at delivery lower than those who presented with paucisymptomatic onset. In our study groups, women who underwent chemotherapy during pregnancy had a higher mean gestational age at delivery and did not experience worse neonatal outcomes compared to those who did not undergo chemotherapy. Conclusions: CRC during pregnancy poses unique diagnostic and therapeutic challenges. Collaborative efforts among various medical disciplines are essential to manage CRC during pregnancy.