On March 13, 1985, Pierce scored 22 points, grabbed 9 rebounds, and recorded 6 assists in a win against the Cleveland Cavaliers.

[6] Pierce and the Bucks would go on to beat Michael Jordan and the Bulls 3–1 in the first round of the playoffs, before being upset by the lower seeded Philadelphia 76ers in the Eastern Conference Semifinals.

[7] Pierce won the NBA Sixth Man of the Year Award for 1986–87 for averaging 19.5 points per game with a 53.4% shooting percentage in his third season with the Bucks.

[8] During the 1989 NBA Playoffs, on May 2, Pierce led the Bucks to 117-113 Game 3 victory over the Atlanta Hawks with a team-high 35 points.

The following season, Pierce earned the Sixth Man award again, averaging 23.0 points per game without starting a single one (an NBA record)[10] in 1989–90.

That season, on November 9, 1989, Pierce played a key role in the longest game in the shot clock era, at four hours and 17 minutes, scoring a team leading 36 points on 15 of 21 shooting, during a 155-154 5OT win.

[16] In the 1993 NBA playoffs, Pierce led the Sonics to 103-100 Game 7 win in the conference semifinals over the Houston Rockets with a game-leading 25 points.

[17] In the next round, Pierce, alongside teammates Gary Payton and Shawn Kemp, lost in seven games to the Phoenix Suns, narrowly missing an NBA Finals appearance.

On July 18, 1994, Pierce was traded along with Carlos Rogers and two draft picks to the Golden State Warriors in exchange for Byron Houston and Sarunas Marciulionis.

In February, with the Nuggets out of the playoff picture, Pierce was traded to the Charlotte Hornets for Anthony Goldwire and George Zidek.

Since retiring, Pierce has developed his own basketball system that assists with shooting accuracy with specially-designed fingertip-placement markers.

[23] Pierce returned to Rice University to complete his degree, and graduated with a Bachelor of Arts in kinesiology in May 2012.