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In #8181 (comment), it looks like there's consensus for dropping Python 3.5 in pip 21.0 (January 2021).
As has been done previously, this adds a deprecation warning when running pip on Python 3.5.
It's not urgent, but this could be included in tomorrow's 20.2.3 release (#8511 (comment)), which would give two more months of warning than waiting for pip 20.3 in October.
If so, need to change the message from past to future tense, for example:
Also updated
gone_in
for 2.7 (#6148 (comment)).