In the mid 1990s, Cutty Sark station was proposed as part of a 4.2-kilometre (3 mi) southern extension of the DLR to Lewisham.

[8][9] However, Cutty Sark was dropped from the project owing to its high construction costs (around £50 million) for the private consortium that would design, build, finance and maintain the extension.

[14][15][16] When escalators are unavailable, passengers must use a 121-step staircase (or a small lift) to enter and leave the deep-level station.

[17][9] A local Labour councillor accused CGL Rail of handing the station back to TfL in a "shameful state".

[20] In February 2025, TfL announced that the station would close temporarily to allow all four escalators to be replaced at a cost of £4 million.

While most on the network have had their platforms extended as part of Transport for London's three-carriage capacity enhancement project, the two-car-long island platform at Cutty Sark cannot be lengthened due to cost (estimated at £30m) and risk of damage to the heritage site at street level.