| HINT | ANSWER | Extras |
| Year Pirates were founded | |
| What was the first World Series that the Pirates played in? | |
| What was the first World Series Win for the Pirates? | |
| Who had a walk of homerun in the 1960 World Series? | |
| Which World Series wins was 'Roberto Clemente' a part of for the Pirates? | |
| What are the Pirates World Series record? (W-L) | |
| On July 12, 1997 the Pirates became the only team to 'No-Hit' a team through extra innings. Name the starting pitcher responsible. | |
| On the previously mentioned game, who closed the game for the Pirates? | |
| What deficit did the Pirates recover from to win their second and fifth World Series titles? (L-W) | |
| Who are the Pirates AAA affiliates? | |
| Who are their AA affiliates? | |
| For the next few questions, state the name of the player belonging to the retired player. #1 (Manager) | |
| # 4 (Outfielder) | |
| #8 (Outfielder/First Basemen/Coach) | |
| #9 (Second Basemen/Coach) | |
| #40 (Infielder/Coach/Manager) | |