Kendricks also competed for the Badgers track team in 2007. At the Big Ten Indoor Championships, he placed 12th in the triple jump. He also participated in the long jump event at the Big Ten Conference, where he took 21st.

Kendricks attended the University of Wisconsin–Madison, where he played on the Wisconsin Badgers football team from 2007 to 2010. As a senior in 2010, he was a finalist for the John Mackey Award, received first-team All-Big Ten honors, and was recognized as a consensus first-team All-American.

On June 29, 2011, he signed a contract with the Rams. He made his NFL debut on September 11, 2011, catching one pass for 18 yards against the Philadelphia Eagles. On October 4, 2012, he recorded his first career touchdown on a 7-yard pass from Sam Bradford against the Arizona Cardinals. On March 11, 2015, the Rams signed Kendricks to a four-year, $18.5 million contract extension that included $10 million guaranteed. However, he was released by the Rams on March 10, 2017.

On March 11, 2017, the Green Bay Packers signed Kendricks to a two-year, $4 million contract that included a $1.2 million signing bonus. On September 10, 2017, in his Packers debut, he had 2 receptions for 18 yards against the Seattle Seahawks. On September 24, 2017, Kendricks caught his first touchdown with the Packers on a 1 yard pass from quarterback Aaron Rodgers in a 27–24 win over the Cincinnati Bengals. On October 7, 2018, he caught his first touchdown of the 2018 season from Rodgers in a 31–23 loss to the Detroit Lions.

Kendricks was stopped for a speeding violation in the early morning hours of September 2, 2017, while heading back to Green Bay from a Wisconsin Badgers football game. He was let go with a warning, but a citation for marijuana possession was issued in December 2017 as a result of a search during the traffic stop. The citation was dismissed in October 2018 but later that month, Kendricks was charged with misdemeanor marijuana possession. In January 2019, an attorney for Kendricks entered a not guilty plea on his behalf. Kendricks later pled no contest and was sentenced to six months probation, with the charge to be dropped if eight hours of community service was completed.

On July 24, 2019, Kendricks was signed by the New England Patriots. He was suspended the first game of the season for violating the league’s policy on substances of abuse. He was released from the Patriots on September 9, 2019.

On September 17, 2019, Kendricks was signed by the Los Angeles Chargers.