A prescription for exhibiting the bug
$ mkdir -p t/test-1 t/test-2 t/test-3
$ emacs -Q -nw
M-x eshell
type cd t/<TAB>
expands to 'cd t/test-3'
pressing repeated <TAB>s does not cycle t/test-1, t/test-2, t/test-3
Expected behavior (consistent with emacs 24.2): that the first <TAB> expand to one of t/test-3, and repeated <TAB>s cycle amongst 't/test-1', 't/test-2', and 't/test-3'.