During the late 1990s and 2000s, Winthrop established itself as one of the most successful mid-major programs in college basketball, reaching the NCAA Tournament eight times in 10 seasons.

[2] Since 2009, Winthrop has defeated over 30 non-conference D1 teams including: Auburn (SEC), Clemson (ACC), Wake Forest (ACC), East Carolina, East Tennessee State, Furman, Georgia Southern, Illinois (Big 10), James Madison, Manhattan College, Ohio University, #18 Saint Mary's in 2019, St. Louis, UNC Greensboro, Portland, San Diego, Washington (PAC 12), and William & Mary.

In Winthrop's second season as a Division I program, he led the 4th seeded eagles to their first Big South tournament victory.

WU athletic director Tom Hickman reportedly said that Kenney "graduated his players, ran a clean, upstanding program and did everything first class but had to be relieved of his coaching duties because the school could no longer carry his losing record.

Winthrop appeared in seven NCAA Tournaments, posted six 20-win seasons, and averaged 21.5 victories per year during the Marshall Era.

[10] Under Kelsey, the Eagles' style of play exhibited a fast-paced, high scoring offense and pack line defense.

Kelsey's Eagles broke multiple school records in categories such as free throw accuracy, blocked shots, three-pointers made, offensive pace,[11] and points scored in a single game.

[12] With the help of assistant coaches like Brian Kloman,[13] Kelsey developed a successful local and international recruiting pipeline and signed some of the top players in WU's history.

The Eagles posted a perfect 14–0 mark in conference play, winning the Big South regular season championship.

Notable regular season non-conference victories included wins against Mississippi State and Old Dominion.

Each of Winthrop's four regular season losses came at the hand of a Top 25 opponent, with two of the games decided by single-digit margins.