So far there's one known and confirmed date that Jimi Hendrix played with the Drifters - the Lovers (aka the Squires) with Jimi on bass were photographed on stage with the Drifters at this concert: 

Saturday 26 February 1966
"Winter Weekend", Memorial Chapel, Union College, Schenectady, New York
Complete line-up: The Ronettes, The Drifters, The Lovin' Spoonful

The probable line-up for the Drifters on this occasion:

the Drifters:
Johnny Moore - vocals
Charles Thomas - vocals
Gene Pearson - vocals
Johnny Terry - vocals
Bill Davis - guitar

This was the second day of a two day "Winter Festival" weekend during which Jimi played guitar behind Jimmy Soul and the Ronettes and bass with the Drifters.

See Jimi Hendrix at Union College 1966 for more information on the concert and the Drifters personnel.