Are You a Chicago Cubs Expert?


By: Gavin Thagard

6 Min Quiz

Image: Brad Henson Productions

About This Quiz

"Rooting for the Chicago Cubs is not easy, but the best things in life never are." - Dennis Farina

How big of a Chicago Cubs fan are you? Would you consider yourself an expert on the team and its history? Could you pass a quiz on the Chicago Cubs? Here's your chance to find out!

The Chicago Cubs ball club has been playing baseball since the late 1800s, which even predates Major League Baseball. The team has had some success over the years, but it's also had disappointing droughts that have left fans weary of supporting the team. After all, the team holds the record for failing to reach the NL pennant for 71 years and failing to reach the World Series for 108 years. That means that nearly two generations of Cubs fans weren't able to celebrate a championship in their city. At least they had Michael Jordan and the Bulls in Chicago. Otherwise, fans might have started rioting. 

If you think you know everything about the long history of the Chicago Cubs, then go ahead and give this quiz a try. There might be a few things in here that will surprise you. Get started and test your Cubs knowledge! 

The Chicago Cubs are part of which league?

As one of two leagues in MLB, the National League is the older of the two. It was founded in 1876.


When did the Chicago Orphans become the Chicago Cubs?

Chicago has undergone multiple name changes since the team was founded. Two other names include the Colts and the White Stockings.


Who did the Cubs lose the 1906 World Series to?

This game pitted two teams from the same city against one another. The Cubs were heavy favorites but lost the series in six games.


When did the Cubs win their first World Series?

In 1907, the Cubs faced the Tigers, who were led by rising star Ty Cobb. Cobb had won the AL batting championship that year, a feat he would accomplish 11 more times.


Who was the manager of the Cubs when they went to three straight World Series from 1906-1908?

Frank Chance was a player-manager for the Cubs. While on the field, he played first base.


What home field do the Chicago Cubs play on?

Wrigley Field is named after William Wrigley Jr. Wrigley rose to prominence as a chewing gum magnate.


How many National League pennants have the Cubs won?

No team has won more National League pennants than the Giants with 23. The team has also won eight World Series.


Who hit the "Homer in the Gloamin'" in 1938?

With darkness quickly approaching and no stadium lights in baseball yet, Gabby Hartnett stepped up to the plate and hit a walk-off home run against the Pirates. The home run gave the Cubs the National League pennant, as they advanced to the World Series.


What position did Gabby Hartnett play?

Playing for the Cubs from 1922 until 1940, Hartnett was an outstanding catcher and batter for the team. He even won the NL MVP in 1935.


Who was the home run leader for the National League from 1926-1928 while playing with the Cubs?

One of the highlights of Hack Wilson's career was his 56 home run season in 1930. This was a National League record until it was surpassed in 1998 by Sammy Sosa and Mark McGwire.


Who did the Cubs lose the 1945 World Series to​?

1945 was the last time the Cubs would advance to World Series until after the turn of the century. They lost the series 4-3.


Who pitched game 2 of the 1938 World Series for the Cubs?

Dizzy Dean had helped carry the Chicago Cubs to the World Series in 1938, but his arm was far from what it once was. He would lose game 2 of the World Series, as the Yankees went on to sweep the Cubs.


What was Ernie Banks' nickname?

Ernie Banks played for the Cubs from 1953 until 1971. During that time, he went to 14 All-Star games and was a two-time NL MVP.


When did Ernie Banks win his first NL MVP?

Banks won back to back MVP awards in 1958 and 1959. He was the first NL player to accomplish this.


What number did Ernie Banks wear?

Banks had his number 14 retired by the Cubs. He was the first Cubs' player to receive this honor.


Who did Ernie Banks beat out of the 1960 NL home run title?

Hank Aaron was the first player to beat Babe Ruth's career home run record. He finished his career with 755 home runs.


What year was Hank Sauer both the NL MVP and home run leader?

Hank Sauer only played seven seasons with the Cubs, but it was probably the most successful stint of his career. During that time, he went to two All-Star games, including​ an outstanding 1952 season.


Who did the Cubs trade Lou Brock for in 1964?

This was one of the worst trades in baseball history. Lou Brock would go on to have a hall of fame career with the Cardinals, while Ernie Broglio would only play a few more seasons with the Cubs.


What position did Ron Santo play?

Ron Santo was elected to the hall of fame in 2012, two years after his death. His number 10 was retired by the Cubs.


Where was Ron Santo traded to for the last season of his career?

Ron Santo was a five-time Golden Glove Award winner. He was also elected to nine All-Star games.


Who bought the Chicago Cubs in 1981?

The Wrigley family owned the Cubs for 65 years. Few families are as well associated with a team as they were.


What position did Rick Sutcliffe play?

Rick Sutcliffe was nicknamed "The Red Baron." He got the name because of his red-tinted beard.


What year did Rick Sutcliffe win the Cy Young Award?

1984 was Sutcliffe's first year with the Cubs. He had been traded from the Cleveland Indians prior to the season.


Which Cubs player was named NL Rookie of the Year in 1998?

In 1998, Kerry Wood threw 20 strikeouts in a game against the Astros. This is tied for the MLB record.


Who was named NL MVP in 1998?

Sammy Sosa was a dominant home run hitter throughout his career. However, that career is tarnished by his association with steroids.


What position did Sammy Sosa play?

Sammy Sosa surpassed the single-season home run record in 1998. However, that same season, Mark McGwire passed Sammy Sosa, setting the record himself.


Who did the Chicago Cubs play in the 2003 NL Championship Series?

The Cubs lost game 1 against the Marlins, but they then took a 3-1 lead. However, the team collapsed in the final three games and lost the series 4-3.


What's the name of the fan who deflected the ball away from the glove of Moises Alou in the 2003 NL Championship Series?

Steve Bartman has been heavily criticized by the Cubs' fanbase. So much so, that he stopped coming to games.


When did Joe Maddon take over as manager of the Chicago Cubs?

Joe Maddon was a coach for the Los Angeles Angels when they won the World Series in 2002. That team defeated the Giants in seven games.


Who was the NL Rookie of the Year in 2015?

Kris Bryant hit his first home run in Major League Baseball on May 9, 2015. The home run was hit off Kyle Lohse, who played for the Brewers.


Who did the Cubs defeat in the 2016 World Series?

This was the Cubs' first World Series title in 108 years. It ended what many considered to be a curse in the town.


The Cubs came back in the 2016 World Series after being down by how much?

This was the first time a team came back after being down 3-1 since the Royals did it in 1985. Adding to the odds, the Cubs had to win the last two games on the road.


Who was the MVP of the 2016 World Series?

Ben Zobrist joined the Cubs prior to the 2016 season. This was after he played with the Kansas City Royals in 2015, the year in which they won the World Series


How many games did the Cubs vs Nationals matchup last in the 2017 NLDS?

The Cubs defeated the Nationals 3-2 in the NLDS. This kept the team's hope of defending their World Series title alive.


Who did the Cubs play in the 2017 NLCS?

The Dodgers ended the Cubs' hope of repeating as champions during the NLCS. However, they went on to lose to the Astros in the World Series.


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