We still don't know too much Anko's real powers or abilities in a fight. Still, treating Anko as just a slightly above average Jounin it could very be a tie if Shino is given time to plan and has information on her weaknesses (whatever they be) etc.
Once again Anko is underated, due to the fact we aint seen her full power.
She has the Cursed Seal of Heaven need i say more.
She is a Fire Release user, this is an advantage for shino's bugs.
I got many more reasons on why she would win.
Come on. Anko has a suicide snake technique, a useless curse seal (and apparently useless fire too). Shino is a bug boss and an insect icon. His swarm eats all of Anko's chakra and she's done. Everyone knows most k11 are stronger than fodder jonin.
rofl...serious @ this thread? *sigh* a part of me wishes oro would have given shino the curse mark and trained him also...he'd actually USE IT. anyway, i think shino wins...i guess high dif because of her rank