Modern enhanced recovery protocols discourage drain use due to negative impacts on patient comfort, mobility, and recovery, and lack of proven clinical benefit. After oesophagectomy, however, drains are still routinely placed. This review aimed to assess the evidence for, and how best to use chest drains after oesophageal surgery. A systematic literature search was performed in Medline, Embase and Cochrane collaboration databases. Studies reporting outcomes for different types or uses of thoracic drainage, or outcomes related to drains after trans-thoracic oesophagectomy were included. Studies were collated into domains based on variations in number, position, type, removal criteria, diagnostic use and complications of drains. Methodological quality was assessed with Newcastle-Ottawa and Jadad scores. Among 434 potentially relevant studies, 27 studies met the inclusion criteria and these included 2564 patients. Studies that examined the number of drains showed pain reduction with a single drain compared to multiple drains (3 studies, n = 103), and transhiatal placement compared to intercostal (6 studies, n = 425). Amylase levels may aid diagnosis of anastomotic leak (9 studies, n = 888). Narrow calibre Blake drains may effectively drain both air and fluid (2 studies, n = 163). Drain removal criteria by daily drainage volumes of up to 300mL did not impact subsequent effusion rates (2 studies, n = 130). Complications related directly to drains were reported by 3 studies (n = 59). Available evidence on the impact of thoracic drainage after oesophagectomy is limited, but has the potential to negatively affect outcomes. Further research is required to determine optimum drainage strategies.