Okay, 20 times I decided to play this and keep score. One point for him if he guessed it on first try, half a point each if he failed before he got it right, a point for me if he failed altogether; limiting my choices to fictional characters or real people who are known well enough.
Round one: Akinator 1-0 Vegosiux
He guessed Viconia.
Round two: Akinator 1.5-0.5 Vegosiux
He guessed the Overlord, after failing once.
Round three: Akinator 1.5-1.5 Vegosiux
He didn't guess Coach Oleander.
Round four: Akinator 2-2 Vegosiux
He guessed Anze Kopitar, after failing once.
Round five: Akinator 2-3 Vegosiux
He didn't guess Captain Kaff Tagon.
Round six: Akinator 3-3 Vegosiux
He guessed Josip Broz Tito.
Round seven: Akinator 3.5-3.5 Vegosiux
He guessed Yukari Tanizaki, after failing once.
Round eight: Akinator 4.5-3.5 Vegosiux
He guessed Oliver Cromwell.
Round nine: Akinator 5-4 Vegosiux
He guessed Nick Cave, after failing once.
Round ten, HALFTIME SCORE: Akinator 6-4 Vegosiux
He guessed Katarina du Couteau.
Round eleven: Akinator 7-4 Vegosiux
He guessed himself.
Round twelve: Akinator 8-4 Vegosiux
He guessed Mitsuru Kirijo.
Round thirteen: Akinator 8-5 Vegosiux
He didn't guess Grand Duchess Letopanyu Beneej Spoor; nor did he actually know her.
Round fourteen: Akinator 9-5 Vegosiux
He guessed Asterix.
Round fifteen: Akinator 10-5 Vegosiux
He guessed Werner Heisenberg...but for some reason he had to ask meif he was a Japanese pop singer 0.o.
Round sixteen: Akinator 11-5 Vegosiux
He guessed The Childlike Empress.
Round seventeen: Akinator 11.5-5.5 Vegosiux
He guessed Etna, after failing once.
Round eighteen: Akinator 12.5-5.5 Vegosiux
He guessed Nikola Tesla.
Round nineteen: Akinator 13-6 Vegosiux
He guessed Wayne Gretzky, after failing once.
Round twenty: Akinator 14-6 Vegosiux
He guessed Annah.
Well, the final tally, he beat me 14-6, but at least I held my ground for a while!