| Hint | Answer | Extra Info |
| Main player of note acquired for Lou Brock | |
| This manager once played for the Cubs in one game as a pinch runner | |
| This Cubs Closer has a son named Blaze | |
| Eamus Catuli rougly translates to | |
| Team Cubs last played in the World Series | |
| Babe Ruth's called shot occurred in which inning | |
| Pitcher Called Shot was hit off of | |
| This player hit a HR right after Babe Ruth's called shot | |
| Famous Bar near Wrigley Field owned by the Loukas family | |
| Kiki Cuylers real name | |
| Notorious umpire during Merkle's Boner | |
| This manager was nicknamed The Lip | |
| Mark Prior came from this college | |
| Stadium Cubs played at before Wrigley Field | |
| Largest Game Attendance was close to 51,000 because of | |
| 'The Peerless Leader' | |
| The Cubs once held Spring Training at this wet coast location | |
| This pitcher had many superstitions including hopping over foul lines, brushing teeth between innings, eating licorice | |
| This 2B was part of the trade for Aramis Ramirez | |
| Dimension of Wrigley Field in Centerfield | |
| This Cubs reliever had too many fingers | |
| This Cub once hit a HR that hit a building across the street | |
| This guy wrote Go Cubs Go and A Dying Cubs Fans Last Request | |
| This manager is most famous for his postgame rant | |
| The date the Cubs last won the World Series | |