These are some of my favorite match-ups that I'd HOPE they happen if Season 6 would be released. Feel free to share yours in the comments! :D
Season 6 (1st Half)
Premiere: Mark Zuckerberg vs. Alexander Graham Bell
Episode 2: Mr. Bean vs. Charlie Chaplin vs. Jim Carrey
Episode 3: Jimi Hendrix vs. Kurt Cobain
Episode 4: JK Rowling vs. Jane Austen
Episode 5: Phoenix Wright vs. Atticus Finch
Half-Finale (Episode 6): Three Musketeers vs. Three Stooges
Season 6 (2nd Half)
Episode 7: Rocky Balboa vs. Benito Mussolini
Episode 8: Conan the Barbarian vs. Conan O' Brien
Episode 9: Freddy Krueger vs. Wolverine
Episode 10: Mother Teresa vs. Sigmund Freud
Episode 11: Usain Bolt vs. The Flash
Finale: Johann Sebastian Bach vs. Tupac vs. Eminem