Cheeks was born in Chicago, and attended DuSable High School. He attended West Texas State University from 1974 to 1978. Cheeks was an all-Missouri Valley Conference player for three straight seasons, as he averaged 16.8 points per game and shot nearly 57% for his collegiate career. He is currently the third leading scorer in WTSU/WTAM history.
Through his mother, he is a part of the Conley family of the Tennessee Valley.
After college, Cheeks was selected as the 36th pick in the second round of the 1978 NBA Draft by the Philadelphia 76ers. Cheeks played 15 years as a point guard in the NBA, including 11 with the Philadelphia 76ers, He earned four trips to the NBA All-Star Game, and he helped the 76ers earn three trips to the NBA Finals in a four-year span in the early 1980s (1980, 1982, and 1983), including one NBA championship in 1983. While starting at point guard for a Sixers team that at times included stars such as Julius Erving, Moses Malone, Andrew Toney, and Charles Barkley, Cheeks was well regarded for his unselfish team play and excellent defensive skills. As a result, he was named to four straight NBA All-Defensive squads from 1983 to 1986, and then earned a spot on the second team in 1987.
In NBA history, Cheeks ranks fifth all-time in steals and eleventh all-time in assists. At the time of his retirement from the NBA in 1993, Cheeks was the NBA all-time leader in steals and ranked fifth all-time in assists. He averaged 11.7 points per game for his career and notched over 2 steals per contest.
After retirement, Cheeks spent one year coaching in the Continental Basketball Association, before becoming the 76ers assistant head coach in 1994. He coached under head coaches John Lucas (1994–96), Johnny Davis (1996–97), and Larry Brown, and he was an instrumental part of the Philadelphia team that reached the 2001 NBA Finals. In 2001, he was hired as Portland Trail Blazers head coach. He led the team to two playoff berths in four years as coach, but could not get past the first round. He was fired after a poor start to the 2004–05 campaign.
On April 25, 2003, during a game between the Trail Blazers and the Dallas Mavericks, Cheeks aided 13-year-old Natalie Gilbert in singing the American national anthem. After Gilbert forgot the words at "At the twilight's last gleaming", Cheeks rushed over to help her and they finished it together, as the entire Rose Garden Arena crowd sang with them. Cheeks and Gilbert received a standing ovation after the song was over.
In 2005, Cheeks was named as head coach of the 76ers. Maurice Cheeks was popular among Sixers fans because of his eleven-year tenure with the Sixers, during which he helped guide the Sixers to the 1983 NBA championship. The move was also praised by Sixers star Allen Iverson, who worked with Cheeks during his run as Sixers' Assistant Head Coach.
However, he missed the playoffs in each of his first two seasons. Frustrations began to grow with Sixers veterans Allen Iverson and Chris Webber, who were not happy with the team's direction. During the 2006-07 season, Iverson would be traded to the Nuggets and Webber would be released, leaving Cheeks with one of the youngest teams in the NBA. On February 20, 2007, the 76ers extended Cheeks' contract one year despite his losing record as coach.
At the beginning of the 2007–08 season, expectations were low and the 76ers were picked to finish last in the Conference by many prognosticators. However, the Sixers clinched a playoff berth with a win over the Atlanta Hawks on April 4, 2008. It was their first postseason appearance since 2005, as well as the first in the post-Iverson era. However, they were eliminated by the Detroit Pistons, 4–2. Even with this elimination, many fans considered this to be a successful season, considering that the Sixers were 12 games under .500 in early February and went on to have a 21-7 run that led them to the playoffs.
The Sixers started out the 2008-09 NBA season 9-14, despite their signing of Elton Brand and re-signing of Andre Iguodala during the offseason. Due to their slow start, the 76ers fired Cheeks on December 13, 2008.