Michigan State Gregory was an assistant at
Michigan State for five years, from 1999 to 2003, under head coach
Tom Izzo. During that time, the Spartans reached the
Final Four three times and won the
2000 national title.
Dayton On April 9, 2003, Gregory was named the head basketball coach of the
Dayton Flyers. As Flyers head coach, he led the team to the
2004 and the
2009 NCAA tournaments as well as the
2008 National Invitation Tournament. On January 14, 2008, Gregory led the Dayton Flyers to a top-14 ranking in the
AP poll. This was the highest ranking for Dayton in 40 years. He capped off the
2009–10 season by leading the Flyers to the
2010 NIT championship over
North Carolina. Gregory had a 172–94 record with the Flyers over eight seasons and NCAA Tournament appearances.
Georgia Tech On March 28, 2011, it was announced that Gregory would become the 13th head coach at
Georgia Tech replacing
Paul Hewitt. Gregory struggled at Georgia Tech, only finishing above .500 two times. He failed to make a postseason appearance in his first four years at Georgia Tech. On March 16, 2015, Georgia Tech announced that Gregory would continue as head basketball coach for another year, despite the fact he never had a conference finish higher than ninth. In the
2015–16 season, Georgia Tech improved, finishing the season 21–15 and did receive a bid to the
National Invitation Tournament, their first postseason trip under Gregory. The Yellow Jackets won two games before losing in the quarterfinals. After a 5th consecutive losing record in the ACC, Georgia Tech Athletic Director
Mike Bobinski announced on March 25, 2016, that Gregory would not return for the 2016–17 season. His record was 76–86 overall and 27–61 in ACC play.
Michigan State Gregory served as a consultant to his old head coach Tom Izzo at Michigan State during the 2016–17 season.
South Florida On March 14, 2017, Gregory was hired as head coach at South Florida to replace
Orlando Antigua. USF went 10–22 in Gregory's first season, which was the first time the program posted ten wins since the 2014–15 season—the first of the Antigua era. It posted a 7–11 record at the
Yuengling Center (formerly the USF Sun Dome), but struggled away from home, collecting just three wins away from Tampa. The Bulls finished 3–15 in AAC play, last in the conference and was a first-round exit in the 2018 conference tournament. Gregory welcomed nine new players to the program for the 2018–19 season. USF also was benefitted by
Gardner–Webb transfer Laquincy Rideau, who came off a
redshirt season in 2017–18 and
Alexis Yetna's addition to the hardwood. It started the season 10–2 through non-conference play before going 8–10 in AAC play. Under Gregory's eye, Rideau earned an AAC Defensive Player of the Year honor, while Yetna was named the league's Freshman of the Year for their efforts during the regular season. Although it was bounced in the first round of the conference tournament yet again, this time by
UConn, USF received a bid to play in the
College Basketball Invitational, the third tier postseason college basketball tournament. The Bulls came back from a 25-point deficit to defeat
Stony Brook in the first round before defeating
Utah Valley and
Loyola Marymount to reach the CBI finals. In a three-game series against
DePaul, the Bulls took two-of-three (63–61, 96–100 OT, 77–65) to win the tournament. Sophomore guard David Collins was named as the tournament's MVP. In the process, USF finished 24–14 and had the largest improvement among
NCAA Division I teams. Three Bulls—Rideau, Collins and Yetna—were named preseason all-conference selections before the 2019–20 season. Yetna, who had battled a leg injury and rehabbed over the previous summer, suffered a devastating knee injury in practice prior to the team's season opening game against
Arkansas–Pine Bluff and was ruled out for the season. Former
LSU transfer
Mayan Kiir left the team as well, turning the Bulls into one of the largest teams in the AAC to one of the smallest teams in the conference. As a result, the Bulls struggled offensively and failed to reach 70 points in 24 in 31 of their games. However, USF was extremely strong on the defensive side of the court, ranking 20th in the NCAA in scoring defense (62.7 PPG), while holding 27 of its 31 opponents under their season scoring average at the time of play. USF failed to put together a second straight winning season under Gregory, going 14–17 and 7–11 in AAC play. The Bulls were slated to play
War on I-4 rival
UCF in the first round of the conference tournament before the conference announced the cancelation of the game due to the
COVID-19 pandemic, just 65 minutes before tipoff between the Bulls and Knights. Over the extended break caused by the coronavirus, the Bulls added length and saw the return of Yetna to the starting rotation. Former
Mississippi State power forward Prince Oduro and
Texas Tech center Russel Tchewa joined the squad and the Bulls brought in consensus four-star combo guard Caleb Murphy to bolster a team that just lost two seniors and one outgoing transfer. USF was picked to finish 5th in the AAC in the 2020–21 season. Gregory won his 300th career game as a head coach on December 12, 2020, against
Wofford. It was announced, on January 4, 2022, that Gregory's contract would be extended until the 2025–26 season, as a part of 14 overall head coach extensions executed by USF Vice President of Athletics Michael Kelly. After enduring a fourth straight losing season, on March 10, 2023, Gregory was relieved of his duties as South Florida head coach. ==Front office==