During the 2006 offseason, the Pistons offered Ben Wallace a four-year, $48 million contract which would have made him the highest-paid Piston ever . However, Wallace agreed to a 4-year, $60 million contract with the Chicago Bulls.

To replace Ben Wallace, the Pistons signed Nazr Mohammed as a center. He struggled to fill the team's void at center, however, and the team began looking for additional help. On January 17, the Pistons signed Chris Webber, who had become a free agent. The Pistons quickly began playing better basketball and, according to Newsday, started "to get their swagger back."The Pistons were only 21–15 before Webber was acquired; with him, the team went 32–14. On April 11, the Pistons clinched the best record in the Eastern Conference, which guaranteed them home-court advantage for first three rounds of the playoffs.

The Pistons opened the 2007 NBA Playoffs with a 4–0 victory over the Orlando Magic, their first playoff series sweep since 1990. The team advanced to face the Chicago Bulls, marking the first time that the Central Division rivals had met in the postseason since 1991. After winning the first two games by 26 and 21 points, the Pistons overcame a 19-point deficit to win Game 3, 81–74. Chicago avoided elimination by winning Games 4 and 5, but the Pistons closed out the series, 95–85, in Game 6. They advanced to the Eastern Conference Finals for the fifth consecutive time (equaling their streak from 1987–1991) - one short of the NBA record set by the Los Angeles Lakers in the 1980s. In the Eastern Conference Finals, the Pistons won games 1 and 2, but lost 4 in a row to the Cavaliers.

Following the season, the Pistons traded Carlos Delfino to the Toronto Raptors in exchange for 2009 and 2011 second-round draft picks. In the 2007 NBA Draft the Pistons selected Rodney Stuckey as the 15th overall pick and Arron Afflalo as the 27th overall pick. They also re-signed Chauncey Billups to a long-term contract, as well as re-signing top prospect Amir Johnson and key reserve Antonio McDyess. This season will mark the 50th anniversary of the franchise in Detroit, so The Palace of Auburn Hills floor was given a retouch, as the 50th anniversary logo was encased on center court, and blue replaced red on the sideline, retaining red on the baseline surrounding the basket with the words "Detroit Pistons." The remainder of the court remained unchanged. This marked the first time since their first season at the Pontiac Silverdome (1978–79) that the sideline of the Pistons floor will be painted blue, as opposed to their traditional red.

At the start of the 2008 season, Rasheed Wallace became the Pistons' new center. Upon entering his third season as Pistons coach, Saunders became the longest-tenured Pistons coach since Chuck Daly's nine-year tenure (1983–92). Detroit finished the season 59–23, with the second-best record in the league. The Boston Celtics held the first seed, and many speculated that Boston was their main competition in the Eastern Conference. In the 2008 NBA Playoffs, Detroit started out poorly with a Game 1 loss to the seventh-seeded Philadelphia 76ers and found themselves in a 2-games-to-1 deficit. But the Pistons rallied to defeat the Sixers in six games.

Meanwhile in the 2008 NBA Playoffs, Detroit rolled out to a Game 1 romp of the Orlando Magic, and won a tight Game 2 amid mild controversy. At the very end of the third quarter, Chauncey Billups hit a three point field goal that gave the Pistons a three point lead. However, the clock had stopped shortly into the play. League rules currently prohibit officials from using both instant replay and a timing device to measure how much time has elapsed when a clock malfunctions, nor is a replay from the time of the malfunction onward allowed. The officials estimated that the play took 4.6 seconds, and since there were 5.1 seconds remaining when it began, the field goal was counted. The NBA later admitted that the play actually took 5.7 seconds and the basket should not have counted

In addition to losing Game 3 badly, 111–86, the Pistons also lost all-star point guard and team leader Chauncey Billups to a hamstring injury. Despite his absence, the Pistons rallied from 15 down in the 3rd quarter to win Game 4 90–89, on a field goal by Tayshaun Prince with just 8.9 seconds to play, taking a 3–1 series lead. Again with Billups sitting on the sideline, they then proceeded to win Game 5 in Detroit, winning the series 4 games to 1.

Detroit advanced to the NBA Conference Finals for the sixth straight season, squaring off against the Boston Celtics. They lost game one 79–88, but won in game two on the road, 103–97 (marking Boston's first home court loss in the post-season). Immediately following that, the Celtics won their first road playoff game of the post-season, 94–80, in game three. Game four saw the Pistons win 94–75. In the pivotal fifth game, they lost 106–102, despite rallying from 18 points down late in the game. In Game 6, the Pistons entered the fourth quarter leading 70–60, but a lack of focus, a poor game from Rasheed Wallace, and a rally-killing turnover by Tayshaun Prince ultimately lead to their demise; the Pistons ended their season with an 89–81 loss. With that, the Celtics went on to win the 2008 NBA Finals. On June 3, 2008, the Pistons announced that head coach Flip Saunders will not return as head coach for the 2008–09 regular season. On June 10, 2008 the Pistons named first year assistant coach and former players union repesentative Michael Curry as their new head coach for the 2008–09 season.