Christy Gregory retires after 23 years as Milford softball head coach

Longtime Milford softball head coach Christy Gregory has announced that she is retiring after leading the Eagles for 23 seasons. Gregory has a career record of 416-194-1 and led the Eagles to their lone state tournament appearance in 2004, just her second season at the helm. Her teams won five outright Eastern Cincinnati Conference titles (2014-2017, 2022) and claimed a share of four more (2018, 2021, 2023, 2024). When Milford beat Anderson on April 10 of this year, Gregory became one of six Southwest Ohio coaches to reach 400 wins, joining Steve Castner (580), Paul Fernandez (565), Brenda Stieger (555), Keith Castner (517) and Blaine Wallace (502 as of May 27, 2026).

After the 2004 season, the only other Milford team to win a district title under Gregory was the 2023 squad that went 22-5. This season, the Eagles went 23-4, including winning 20 of 21 games, but fell to Mason in a district final. The Enquirer will update this story.