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Szczur signed a minor league contract with the Philadelphia Phillies on December 13, 2019, with an invite to major-league spring training camp.

On December 14, 2018, Szczur signed a minor league contract with the Arizona Diamondbacks. He elected free agency on November 7, 2019.

Szczur was designated for assignment by the Cubs on May 6, 2017. The Cubs traded him to the San Diego Padres for RHP Justin Hancock on May 8. He declared free agency on October 2, 2018. In 2018 he batted .187.

On April 29, 2016, Szczur hit his first Major League grand slam against the Atlanta Braves in the 8th inning, putting the Cubs up 6–1. In 2016, Szczur played 107 games batting .259 with five home runs and 24 RBI. Szczur made no appearances during the Cubs World Series run.

Szczur split time during the 2015 season between Triple-A and the Majors, ultimately being called up by the Cubs on seven different occasions.

On August 16, 2014, Szczur was called up to the Cubs. He made his debut with the Cubs the next day. Szczur recorded his first Major League hit on August 21 against the San Francisco Giants and his first career home run on September 13 against the Pittsburgh Pirates

Szczur and his wife, Natalie, were married in November 2014 in Philadelphia, Pennsylvania. They have one child, Matt Jr.

Szczur signed a contract with the Chicago Cubs organization, which drafted him in the fifth-round of the 2010 Major League Baseball Draft. He received a $100,000 signing bonus, with an additional $500,000 if he declined to attend the NFL combine and made a written commitment to baseball before February 10, 2011. He was assigned to the club's short season Class-A team, the Boise Hawks, and first appeared in uniform July 8, 2010. He was then promoted to the club's mid-A team, the Peoria Chiefs on July 27, 2010. He hit .347 in 25 games in 2010.

On July 9, 2011, Szczur was assigned to the Class A-Advanced Daytona Cubs roster. On July 27, 2012, Szczur was promoted to the Double-A Tennessee Smokies. He began the 2014 season with the Triple-A Iowa Cubs before being promoted to the Major League roster.

After the 2010 season, Szczur committed to baseball and signed a $1.5 million deal with the Cubs in January 2011. As he was released from his initial contract and signed a new contract to receive the bonus, he would have been eligible in the 2011 Rule 5 draft if not added to the Cubs' 40 man roster.

In football, Szczur played wide receiver, running back, wildcat quarterback and was a return specialist on special teams. During his junior season, Szczur was a consensus All-American and was named the CAA Offensive Player of the Year as Villanova went on to win its first-ever FCS National Championship. In the 2009 NCAA Division I Football Championship Game, he gained 270 all-purpose yards and was awarded MVP honors.

In 2009, Szczur donated bone marrow to a 15-month-old Ukrainian girl named Anastasia battling leukemia. Szczur essentially saved the girl's life given the severity of her condition and how hard it would have been to find another person that was a match for bone marrow. He met the healthy 4-year-old girl and her parents via Skype using a translator who was present at Anastasia's house. It was documented in E:60 Risking it All, which is one of ESPN's E:60 presentations.

Szczur was born in Cape May Court House, New Jersey, and grew up in the Erma section of Lower Township, New Jersey. He attended Lower Cape May Regional High School, where he earned varsity letters in football, baseball, and track and field. Szczur was drafted in the 2007 Major League Baseball draft out of high school by the Los Angeles Dodgers in the 38th round, but decided to attend Villanova University instead.

Matthew Francis Szczur (/ˈ s iː z ər / ; born July 20, 1989) is an American professional baseball outfielder in the Philadelphia Phillies organization. He made his Major League Baseball (MLB) debut with the Chicago Cubs in 2014 and has also played for the San Diego Padres. Prior to his pro baseball career, Szczur played football and baseball at Villanova University, winning MVP of the 2009 FCS National Championship Game.