Question: When did the Ricketts family acquire a majority interest in the Cubs?
Answer: 2009

Question: Who did Chicago engage in a see-saw battle for first place into August 2009?
Answer: St. Louis

Question: What plagued the Cubs in 2009?
Answer: injuries

Question: Who debuted as the starting shortstop in early May 2010?
Answer: Starlin Castro

Question: When did Starlin Castro debut as the starting shortstop?
Answer: early May (2010)

Question: Who announced on August 22nd they were leaving the Cubs prematurely? 
Answer: Lou Piniella

Question: Why did Lou Piniella leave the cubs prematurely?
Answer: take care of his sick mother

Question: How many games under .500 did the Cubs finish the 2011 season with?
Answer: 20

Question: Who was the new owner of the Cubs?
Answer: Tom Ricketts

Question: Who did the new owner of the Cubs sign from the Boston Red Sox?
Answer: Theo Epstein

Question: How much was the contract given to Theo Epstein worth?
Answer: $18 million

Question: Who did the Cubs trade to the Texas Rangers for Mike Olt, C.J. Edwards, Neil Ramirez, and Justin Grimm?
Answer: Matt Garza

Question: Who did the Cubs send to the New York Yankees for minor leaguer Corey Black?
Answer: Alfonso Soriano

Question: When did Theo Epstein made the decision to fire Dale Sveum?
Answer: September 30, 2013

Question: How many seasons did Dale Sveum spend with the Cubs before getting fired?
Answer: two seasons

Question: When did the Cubs announce that Joe Maddon had signed a five-year contract to be the 54th manager?
Answer: November 2, 2014

Question: Who did the team sign on December 10, 2014 as a free agent?
Answer: Jon Lester

Question: How much was Jon Lester's contract worth?
Answer: $155 million

Question: What was the record the Cubs finished with during the 2015 season?
Answer: 97–65

Question: When were the Cubs and New York Giants involved in a tight pennant race?
Answer: September 23, 1908

Question: Who were the Cubs involved with for a tight pennant race on September 23, 1908?
Answer: New York Giants

Question: Who was the runner on first base?
Answer: Fred Merkle

Question: When was game three of the World Series between the Cubs and the New York Yankees?
Answer: October 1, 1932

Question: Who allegedly hit a home run to the Center?
Answer: Babe Ruth

Question: When did Babe Ruth retire?
Answer: 1935

Question: When did Hack Wilson set a record of 56 home-runs and 190 runs-batted-in?
Answer: 1930

Question: Who Broke Lou Gehrig's MLB record of 176 RBI?
Answer: Hack Wilson

Question: When did Manny Ramirez get his 165 RBI?
Answer: 1999

Question: What was Wilson named by the Baseball Writer's Association of America? 
Answer: "Most Useful" player

Question: When did protesters run into the outfield and try to set fire to the U.S. flag?
Answer: April 25, 1976

Question: What stadium did protesters try to burn the U.S.  flag?
Answer: Dodger Stadium

Question: Who grabbed the flag before protesters could light it on fire?
Answer: Rick Monday

Question: When did Sammy Sosa explode into pursuit of Roger Maris' home run record? 
Answer: 1998

Question: Who was in pursuit of Roger Maris' home run record?
Answer: Sammy Sosa

Question: Sammy Sosa was in pursuit of beating whose home run record?
Answer: Roger Maris

Question: What award did Sammy Sosa win?
Answer: the NL MVP Award

Question: When did the Cubs record their 10,000 regular-season win?
Answer: April 23, 2008

Question: Who did the Cubs record their 10,000 regular-season against?
Answer: Colorado Rockies

Question: When was the beginning of the National League?
Answer: 1876

Question: How many batters did Kerry Wood strike out against Houston?
Answer: 20

Question: When did Kerry Wood strike out 20 batters against Houston?
Answer: May 6, 1998

Question: Kerry Wood struck out 20 batters against what team?
Answer: Houston

Question: What is the longest championship drought in all four of the major North American professional sports leagues?
Answer: 107 seasons

Question: The championship drought has led to the Chicago Cubs being know as what?
Answer: The Lovable Losers

Question: When was the last time the Chicago Cubs appeared in the Fall Classic?
Answer: 1945

Question: When was the last time the Chicago Cubs win a World Series championship?
Answer: 1908

Question: Who was the first and only player to hit a pitched ball onto the roof of a five-story building across Waveland Ave?
Answer: Glenallen Hill

Question: When did the first and only player to hit a pitched ball onto the roof of a five-story building across Waveland Ave?
Answer: May 11, 2000

Question: Who barely missed the scoreboard when he launched a home run ball onto Sheffield Avenue?
Answer: Bill Nicholson

Question: When did the Cubs sign a developmental agreement with the Kane County Cougars?
Answer: 2012

Question: The Cubs had a Class A minor league affiliation on two occasions with who?
Answer: Peoria Chiefs

Question: When did the Cubs announce a move of their top class A affiliate from Daytona to Myrtle Beach?
Answer: September 16, 2014

Question: Who began spring training in Hot Springs, Arkansas in 1886?
Answer: Chicago White Stockings

Question: Who is the founder of Spalding Sporting Goods?
Answer: Albert Spalding

Question: Whittington Park, Majestic Park, and Fogel Field were all built where?
Answer: Hot Springs, Arkansas

Question: Where is the Cubs' current spring  training facility located?
Answer: Sloan Park

Question: How many seats are in the Cubs' Sloan Park training facility?
Answer: 15,000

Question: When did Sloan Park open?
Answer: 2014

Question: Where is Rendezvous Park?
Answer: Mesa

Question: Where is Blair Field?
Answer: Long Beach, California

Question: Between what years did the club hold spring training in Scottsdale, Arizona?
Answer: (1967–1978)

Question: Who had a majority interest in Cataline island  in 1919?
Answer: William Wrigley Jr

Question: What did Wrigley construct on the island to house the Cubs in Spring training?
Answer: a ballpark

Question: When did the Cubs choose to leave Catalina Island?
Answer: 1951

Question: Where was the former location in Mesa?
Answer: the second HoHoKam Park

Question: How many square feet does Fitch Park provide?
Answer: 25,000 square feet

Question: When was the spring training home of the Oakland Athletics built?
Answer: 1976

Question: Who manned the Cubs radio and TV booth for parts of five decades?
Answer: Jack Brickhouse

Question: What was Jack Brickhouse's trademark call?
Answer: Hey Hey!

Question: What did Jack Brickhouse do when he approached his retirement age?
Answer: he personally recommended his successor

Question: How long was Harry Caray's tenure  with the Cubs?
Answer: 17-year

Question: How did Caray become a well-known Chicago figure?
Answer: by broadcasting White Sox games for a decade

Question: How long had Caray been a St Louis Cardinals icon?
Answer: 25 years

Question: Who did Harry hand-pick himself?
Answer: Steve Stone

Question: Who did Caray often playfully quarrel with?
Answer: Stone

Question: Why did Caray often playfully quarrel with Stone?
Answer: over Stone's cigar

Question: What does the crowd sing during the 7th inning to honor Caray's memory?
Answer: Take me out to the ballgame

Question: What company purchased the  Cubs in 1981?
Answer: Tribune Company

Question: How much did Tribune Company purchase the Cubs for?
Answer: $20,500,000

Question: How long were the Cubs ran under the Wrigley family?
Answer: 6 decades

Question: What was "Baseball's Sad Lexicon" also known as?
Answer: "Tinker to Evers to Chance"

Question: Who wrote "Baseball's Sad Lexicon"?
Answer: Franklin Pierce Adams

Question: What poem did Franklin Pierce Adams write? 
Answer: "Baseball's Sad Lexicon,

Question: What is the official Cubs team mascot?
Answer: a young bear cub

Question: What is the official Cubs team mascot's name?
Answer: Clark

Question: When did Clark make his debut?
Answer: January 13, 2014