I can confirm this on a current hardy install.
It is a problem with bash, not bash-completion.
In the given test-case compgen -f does not work correctly:
$ touch "1'1 1" "1'2 2"
$ compgen -f 1\'
1'2 2
1'1 1
$ compgen -f 1\'1
$ echo $?
1
** Changed in: bash (Ubuntu)
Sourcepackagename: bash-completion => bash
Status: New => Confirmed
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tab completion fails when files have same prefix that ends in a
quote/escapable-char
https://bugs.launchpad.net/bugs/123665
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