In his first career game, Billups recorded 15 points, 2 rebounds and 4 assists in 16 minutes of playing time as a reserve in a win against the Michael Jordan-led Bulls.

[8] In his eighth career game, Billups posted a then career-high 22 points, on 5-for-14 shooting from the field and 9-for-10 from the free throw line, to go along with 3 assists and 4 steals, in a 103–99 win over the visiting Raptors.

[10] On February 18, 1998, Billups was traded to the Toronto Raptors, along with Roy Rogers, Dee Brown, and John Thomas in exchange for All-Star point guard Kenny Anderson, Žan Tabak, and Popeye Jones.

[10][11][12] On February 22, in just his second career game with the Raptors, Billups recorded a then-career high of 27 points on 5-for-13 shooting from the field and 13-for-16 from the free throw line, to go along with 2 rebounds and 5 assists in a 113–105 win over the Vancouver Grizzlies.

Three months into his first tenure with the Nuggets, Billups visited a local Denver hospital in order to comfort and inspire Patrick Ireland, a victim of the 1999 Columbine High School Shooting Massacre.

[16] A year later, on February 1, 2000, Billups was traded to the Orlando Magic along with Ron Mercer and Johnny Taylor in exchange for Chris Gatling, Tariq Abdul-Wahad, a future first-round pick, and cash.

[10] In his first career game with the Timberwolves, Billups recorded 15 points, 2 rebounds and 5 assists in a 106–98 road win over the Houston Rockets.

He first made a game winning three on March 9 as time expired to beat the Golden State Warriors 107–105 and Billups scored 31 points.

The Pistons were tied in overtime with the Atlanta Hawks 99–99 until Billups made a top-of-the-key triple with 0.5 seconds left to win the game.

In game 5, Billups played a contributing role in his team's dominating 98–67 victory by scoring 15 points, tied for second on the Pistons.

In the pivotal Game 3 during the first round series against the Milwaukee Bucks, which was tied 1–1, Billups led all scorers with 21 points and finished the scoring for his team by sinking 4 of 4 free throws in the final 31.2 seconds.

These free throws were a key part of the Pistons effort to stave off the Bucks' relentless defense which kept Detroit from scoring a normal field goal during the last 5:34.

[26] Billups helped Detroit win the 2004 NBA Finals over the heavily favored Los Angeles Lakers, 4–1.

The Pistons reached the 2005 NBA Finals but lost in their bid to repeat as champions to the San Antonio Spurs in seven games.

Billups was selected to play as a reserve in the 2008 NBA All-Star Game, along with teammates Richard Hamilton and Rasheed Wallace, an injury replacement.

[31] Billups and the Pistons again made it to the Eastern Conference Finals against the Celtics, but lost the series, 4–2, to the eventual champions.

On November 3, 2008, Billups was traded back to his hometown team the Denver Nuggets along with Antonio McDyess and Cheikh Samb for Allen Iverson.

[32] Pistons GM Joe Dumars said that it was "the hardest and toughest" move he had made as a general manager, describing Billups as "... a guy that I have looked at as a little brother."

Billups chose the #7 jersey to honor Denver Broncos quarterback John Elway, since two of his other favorite numbers, 1 and 4, were already worn by J. R. Smith and Kenyon Martin, respectively.

He joined Magic Johnson, Michael Cooper, Kareem Abdul-Jabbar, and Kurt Rambis as the only players to accomplish this feat since the Boston Celtics of the 1950s and 1960s led by Bill Russell.

On February 5, 2010, Billups set a career high in points with a 39-point performance in a road win over the Los Angeles Lakers with 27 of them coming from 9 three-pointers.

Billups was chosen as the replacement by David Stern for injured New Orleans Hornets point guard Chris Paul at the 2010 NBA All-Star Game.

Despite publicly professing his desire to finish his career in hometown Denver and retire as a member of the Nuggets, Billups was traded to the New York Knicks on February 22, 2011[37] as part of the Carmelo Anthony deal.

Billups indicated that he didn't want to be picked up by a team that was not contending for a championship and said he would retire if he was, pushing the NBA to warn him and his agent that he would be "in breach of his contract" if he did not show up.

[45] Billups helped the Clippers beat Miami, Oklahoma City, Orlando, and the Los Angeles Lakers en route to a 19–9 start.

[59] Coming off the bench, he along with the other new members of the team including All Star Kobe Bryant helped USA go unbeaten at the tournament held in Las Vegas and earn a spot at next Summer Olympics.

In the ensuing three seasons, he began splitting time between the studio and working as a game analyst on selected telecasts.

[72] The Coors Events Center has a large mural of Billups in the northeast corner of the arena as part of his "Chauncey's Kid Roundup" program.

[73] In 1997, Billups and fellow former Celtic Ron Mercer were accused of sexually assaulting a woman at the home of teammate Antoine Walker.

[75] Before he was hired as the head coach for the Portland Trail Blazers, the club asserted that they had investigated this allegation and concluded it did not disqualify him from taking the role.