University of the Cumberlands

6191 College Station Drive Williamsburg, KY 40769

NAIA Kentucky Midwest

Private Small National competitor

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Bailey Dillender

Bailey Dillender is enter her seventh season as head coach of the UC Softball Program after being hired in June of 2017. She is the third head coach in program history and is coming off one of the program's most successful seasons. In 2023, Coach Dillender was named the Mid-South Conference "Coaching for Signifiance" Award winner.

Coach Dillender has guided the Patriots to a record setting season in 2023. UC posted a program record 49 wins, which marked Dillender second 40+ win season after compiling a 49-5-1 record, including a 21-0 record in the Mid-South Conference. The Patriots became the first MSC school to record an undefeated conference regular season and captured the MSC regular season before also winning the Mid-South Conference tournament title. UC went on to host the NAIA Opening Round for the first time in program history, where they notched a 3-0 record to advance to the NAIA World Series. Cumberlands closed out the year ranked third in the NAIA. The Patriots had three NAIA All-Americans (Makenzie Keatts, Talli Burgess, Bailey Turnbow) and four NFCA All-Americans. Keatts was named the MSC Player of the Year, while Burgess earned MSC Pitcher of the Year honors. The Patriots had 12 MSC All-Conference selections and six MSC Gold Glove honors. Coach Dillender was named the MSC Coach of the Year, while Assistant Coach Alyssa Richards was named the MSC Assistant Coach of the Year. The Patriots coaching staff also earned NFCA Regional Coaching Staff of the Year.

For the 2022 season, the Patriots recorded their third straight 30+ wins season after compiling an overall record of 35-16 and 21-7 to finish third in the Mid-South Conference. The team saw two program records broken the season ERA with 2.01 and stolen bases at 108. UC earned eight on the Mid-South All-Conference list with three First Team (Emily Bryant, Maddie SIckua and Hailey Wood), three Second Team (Talli Burgess, Emily Jasper, Kaiti White) and two Honorable Mention (Katie Cheeseman and Morgan Radford). Both Cheeseman and Wood were also honored with MSC Gold Gloves for their play in the field. The Patriots also set a record in the classroom with 23 MSC All-Conference the most in the program’s history.

In the team's 2021 campaign, they earned the program's first 40 win season compiling an overall record of 41-16 with a conference record of 21-9 to finish fourth in the MSC. Dillender helped lead the team to multiple program records including wins (41) and doubles (92) as well as individual season records in the top-five including Talli Burgess with five saves (1st), Maddie Sickau with 51 RBIs (t-1st), and Hailey Wood with 41 stolen bases (third). The Patriots earned plenty of accolades for their historic season including the program's first ever NAIA All-American and NFCA All-American in Sickau who earned second team for both. Sickau also earned NFCA Region VI First Team honors, just the second to make First Team in the program history and Hailey Wood earned Second Team All Region honors. The team had the most on the MSC All-Conference teams in program history with eight, the previous record was six in 2007. Five First Team All-Conference recipients (Burgess, Emily Jasper, Meryn Livingston, Sickau, Wood), a trio of Second Team All-Conference recipients (Emily Bryant, Katie Cheeseman, Kaiti White) and a MSC Gold Glove recipient (Livingston). Also setting records in the classroom with 19 earning MSC Academic All-Conference, the most in UC softball history.

Dillender guided the Patriots 32-21 record, including a 17-11 record in the Mid-South Conference, to enter the 2019 Mid-South Conference Tournament as the third-seed. The Patriots notched several milestones including the 32 wins being the most since 2001, their most conference wins (17) since 2002, and their first winning season since 2008. Cumberlands garnered numerous accolades, including Dillender being named the MSC Coach of the Year, the MSC Freshman of the Year (Maddie Sickau), three First Team All-Conference recipients (Sickau, Hannah Stephenson, Jessica Webb), a pair of Second Team All-Conference recipients (Emily Jasper, Sidney Pennycuff), and a MSC Gold Glove recipient (Maddie Sickau). The Patriots also shined in the classroom as Hannah Stephson was named a CoSIDA Academic All-America, while UC had five Daktronics-NAIA Scholar-Athletes and nine MSC Academic All-Conference honorees.

In her first season as head coach, Dillender led the Patriots to a 17-34 (9-19 Mid-South Conference) record and an appearance in the 2018 Mid-South Conference Tournament. She earned her first MSC Tournament win as the seventh-seeded Patriots knocked off sixth-seeded Pikeville 6-2 on 5/4/18 in Bowling Green, KY. Dillender coached a First Team All-Conference honoree and Gold Glove recipient (Elisa Mauldin), two Mid-South Conference Pitcher of the Week recipients (Sidney Pennycuff, Sydney Maynard), one Mid-South Conference Player of the Week (Tara Comer) and 11 Academic All-Conference honorees.

Prior to joining the Patriots, Dillender spent three years as an assistant coach at Tennessee Tech. She performed a variety of tasks at Tennessee Tech, including conducting individual workouts, recruiting players and field work. Dillender specialized on defense, primarily working with the infielders and catchers. While at TTU, she helped the Golden Eagles to the 2015 Ohio Valley Conference Tournament Championships and an appearance in the NCAA Tournament.

Dillender began her coaching career as an assistant coach at her alma mater Campbellsville. In her two seasons with the Tigers, she helped guide them to an 87-38 record and a share of the Mid-South Conference regular season title in 2013. Her duties included: conducting individual workouts, assisting with hitting and infield, scouting and game management, recruiting and field work.

Prior to starting her coaching career, Dillender was a standout player for four years at Campbellsville. She played in 230 games for the Tigers, finishing her career with a .383 batting average, 269 career hits, 215 RBI's, 55 doubles, and 48 home runs. She garnered MSC Player of the Year honors in both 2010 and 2011, while being a four-time First Team All-Conference selection. Dillender made Mid-South Conference history as she was the first MSC player to earn NAIA Player of the Week accolades. She also garnered NFCA Second Team All-American honors and was a two time NCCAA All-American. Dillender was also a two-time Mid-South Conference Academic All-Conference selection.

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Alyssa Richards

Alyssa Richards has completed her fifth season as an assistant coach for the UC Softball Program after being hired in July of 2017. She works with the pitchers and catchers, while also assisting with the hitters.

The 2022 season proved to be another successful year with Richards on the staff. The team had eight MSC All-Conference winners including three pitchers. Both Talli Burgess and Kaiti White earned MSC Second Team while Morgan Radford earned Honorable Mention. The staff broke the single season ERA record with 2.01. Among the pitching staff UC had three pitchers ranked in the top-five of multiple MSC pitching rankings.

In 2021, Richards was instrumental in the program's best record of 41-16 with a 21-9 conference record to earn fourth in the MSC. She helped coach a pair of pitchers to earn All-Conference honors with Talli Burgess earning First Team and Kaiti White earning Second Team. Richards also helped catcher, Meryn Livingston earn First Team All-Conference honors and a MSC Gold Glove, where she did not commit a single error during the regular season. As a pitching staff, they had an ERA of 2.78, third best in the conference. Burgess also recorded a complete seven inning no-hitter on 4/23/21 against Shawnee State where she struck out six batters and walked zero. The UC pitchers also ranked in the top-three in the MSC in opponent batting average (.242), batters struck out (251) and walks allowed (80). Offensively the team hit a program best 92 doubles with a .312 batting average.

For the 2019 season, Richards assisted in the team's 32-21 record, including a 17-11 record in the Mid-South Conference

to enter the 2019 Mid-South Conference Tournament as the third-seed. Pitcher Jessica Webb earned First Team All-Conference and also recorded two no-hitters on the seasons, coming in back-to-back appearances, the first time in program history. The first one came on 3/11/19 against Asbury with five strikeouts and then recorded her second on 3/13/19 against Hiwassee with six K's. For the season the pitching staff compiled an ERA of 3.59.

The Anderson County, TN product tabbed the first Patriots no-hitter since Whitney Piar delivered a complete game against Alice Lloyd on March 6, 2008. In addition to the first no-hitters of the Dillender coaching era, Webb marked the first time in Patriots history a pitcher penned no-hitters in consecutive appearances in the circle.

In her first season as assistant coach, Richards helped guide the Patriots to a 17-34 (9-19 Mid-South Conference) record and an appearance in the 2018 Mid-South Conference Tournament where they earned a 6-2 victory over sixth-seeded Pikeville on 5/4/18 in Bowling Green, KY. With her experience, she helped increase the record to 32-21 in 2019, highlighted by eight shutouts, team ERA of 3.59 and batting average against of .254.

Prior to joining the Patriots, Richards wrapped up a four-year playing career at Tennessee Tech University where she split time between first base and catcher. Richards played in 209 games, while notching 159 hits, 30 home runs, and 22 doubles over her four-year career at Tennessee Tech. She also recorded 105 RBIs, while posting a .280 career batting average. In 2015, Richards helped lead the Golden Eagles to the Ohio Valley Conference Tournament Championship and was named to the All-Tournament Team. Richards was also named OVC First Team All-Conference during her senior season.

Richards graduated with a Bachelor's degree in Multi-Disciplinary Studies with a focus in Special Education and Physical Education from Tennessee Tech in May 2016. She also graduated with her Master's Degree in Health and Human Performance and Coaching from Cumberlands in May 2021.