Steven Gerrard takes charge of his first competitive game as Ibrox boss against Shkupi, with the return match in Macedonia on Tuesday.
Hibernian start at Easter Road against NSI Runavik of the Faroe Islands, having lost on penalties to Brondby in their last European tie two years ago.
Rangers will face Petrocub of Moldova or NK Osijek in qualifying round two if they progress while Hibs would be up against Asteras Tripolis of Greece.
