The link between thromboembolism and cancer has been recognized for over 100 years. Venous thromboembolism (VTE) is associated with considerable morbidity in patients with cancer, with emerging research also indicating a detrimental effect on survival. Investigations aimed at improving outcomes for patients with cancer have focused on the role of low molecular weight heparin in primary and secondary prevention of VTE and in improving patient survival. Important fundamental questions remain unanswered, however, and a significant line of research needs to be dedicated to investigating VTE in GI cancers. The effect of VTE on survival needs to be clarified, as does the role of anticoagulation in this patient population. Opportunities for additional research include investigating methods to identify patients at risk of developing VTE and developing new strategies and therapeutic interventions to reduce the morbidity and mortality associated with VTE. This review focuses on the current understanding of VTE related to gastrointestinal cancers and directions of interest in research specific to GI cancers and VTE.