Hill was drafted by the Detroit Pistons with the third pick in the NBA draft after graduating from Duke in 1994.[11] He generally played the small forward position during his NBA career.[12] In his first season, he averaged 19.9 points, 6.4 rebounds, 5.0 assists and 1.77 steals per game, and became the first Pistons rookie since Isiah Thomas in 1981–82 to score 1,000 points. Hill ended up sharing NBA Rookie of the Year Award honors with Jason Kidd of the Dallas Mavericks, becoming the first Piston since Dave Bing in 1966–67 to win the award. Hill also won the Sporting News Rookie of the Year Award.[13] He was named to the all-NBA First Team in 1997, and All-NBA Second Teams in 1996, 1998, 1999, and 2000. Hill also regularly played in the NBA All-Star Game, where he made history by being the first rookie to lead an NBA All-Star fan balloting in (1994–95) with 1,289,585 votes,[14] narrowly defeating Shaquille O'Neal. Also, he became the first rookie in any of the four major professional sports leagues to lead all-star fan voting.
In his second season (1995–96), he once again led the All-Star fan balloting, this time edging Michael Jordan (Jordan's first All-Star game after returning since retiring in 1993). During the 1995–96 season, Hill showcased his all-round abilities by leading the NBA in triple-doubles (10). He also won a gold medal at the 1996 Summer Olympics in Atlanta as a member of the U.S. men's basketball team, where he had the team's fifth-highest scoring average (9.7) and led the team in steals (18).[15] In 1996–97 season, Hill averaged 21.4 points, 9.0 rebounds, 7.3 assists, and 1.8 steals per game. He became the first player since Larry Bird in 1989–90 to average 20 points, 9 rebounds and 7 assists in a season, an accomplishment that had not been duplicated until Russell Westbrook averaged a triple-double in the 2016–17 NBA season. Once again, Hill led the league in triple-doubles, where his 13 triple-doubles represented 35 percent of the league's triple-double total that season. He was the league's Player of the Month for January and was also awarded NBA's IBM Award, given to the player with the biggest statistical contributions to his team. He finished third in MVP voting, behind Karl Malone and Michael Jordan.
Much like Scottie Pippen with the Bulls, Hill assumed the role of a "point forward" in Detroit, running the Pistons' offense. As a result, between the 1995–96 and 1998–99 NBA seasons, Hill was the league leader in assists per game among non-guards all four seasons. In the lockout-shortened 1999 season, as he led his team in points, rebounds and assists for the third time, Hill joined Wilt Chamberlain and Elgin Baylor as the only players in NBA history at the time to lead their teams in scoring, rebounding and assists more than once. Hill and Chamberlain were the only two players in league history to lead their teams in points, rebounds, and assists per game three times. Hill was selected to play in the 1998 FIBA World Championship, but in the end, no NBA players played in this tournament due to the lockout.
In the 1999–2000 season, Hill averaged 25.8 points while shooting 49% from the field, the season's third-highest scoring average, behind MVP Shaquille O'Neal and Allen Iverson. He averaged 6.6 rebounds and 5.2 assists per game. However, despite Hill's accomplishments in Detroit, the Pistons never made it far in the playoffs, either losing in the first round (1996, 1997 and 1999), or missing the playoffs entirely in the 1994–95 and 1997–98 seasons. The 2000 playoffs would be no different. On April 15, 2000, 7 days before the start of the playoffs, Hill sprained his left ankle in a game against the Philadelphia 76ers. He continued to play until the first-round playoff series against the Miami Heat, in which his injured ankle got worse, and Hill was forced to leave halfway through game 2. Eventually, the Heat swept the Pistons, 3–0. Hill was initially selected for the 2000 Olympics U.S. team, but could not play due to the ankle injury. That ankle injury would prove to be a major liability for many years to come.[16]
After the first six seasons of his career, before the ankle injury, Hill had amassed a total of 9,393 points, 3,417 rebounds, and 2,720 assists. Oscar Robertson, Bird, Luka Doncic and LeBron James are the only four players in league history to eclipse these numbers after their first six seasons.