In 1987, Bailey graduated from Morgantown High School in Morgantown, West Virginia. He was an All-America nose guard and an all-state center for the Mohigans in 1986.
Bailey is an alumnus of the University of Tennessee and a former defensive tackle on the Volunteers football team. He was a four-year letterman for Johnny Majors and was a member of the 1989 and 1990 Southeastern Conference championship teams. As a junior, Bailey led the Volunteers in sacks and tackles for loss. While he was at Tennessee, the Volunteers participated in the 1988 Peach Bowl, 1990 Cotton Bowl Classic, 1991 Sugar Bowl, and the 1992 Fiesta Bowl. Bailey graduated in 1992 with a Bachelor of Arts in sociology.
Bailey began his coaching career in 1993 as a graduate assistant at West Virginia University under head coach Don Nehlen. He worked with the defensive secondary and in strength and conditioning. During his first year in Morgantown the Mountaineers went undefeated and won the Big East Conference championship. In 1994, Bailey worked with a secondary that led the Big East in interceptions. He coached in the 1994 Sugar Bowl and the 1995 Carquest Bowl.
Bailey served as the defensive ends coach at the Virginia Military Institute from 1995 to 1997. While at VMI He developed the Keydet defensive line into one of the best in the Southern Conference and guided two of his pupils into post-season recognition.
Bailey coached at the University of Louisiana at Lafayette for five seasons under three different head coaches—Nelson Stokley, Jerry Baldwin, and Rickey Bustle. He served as linebackers coach in 1998 and defensive tackles coach from 1999 to 2002. The Ragin' Cajuns led the Sun Belt Conference in sacks during the 2001 football season. They also led the conference in punt returns for the 2001 and 2002 football seasons.
In 2003, Bailey served as defensive line coach at Middle Tennessee State University for Andy McCollum. He improved a defensive line that had finished nearly last in every statistical category the year before, to the top three in sacks, tackles for loss, and quarterback hurries.
Bailey became the defensive line coach at Oklahoma State University in February 2004, where he worked for head coach Les Miles. While at OSU, the Cowboys finished the 2004 season leading the Big 12 Conference in turnover margin, turnovers gained, fumbles recovered and earned a berth in the 2004 Alamo Bowl. While at OSU, Coach Bailey recruited Ryan McBean to the Cowboys. Ryan McBean was the last Oklahoma State defensive lineman to be drafted to the NFL since 2007.
Bailey was the defensive line coach at the University of Minnesota from 2005 to 2006, where he worked under Glen Mason. In his first year at Minnesota, three of his pupils earned All-Big 10 honors which included the Big 10 Conference Defensive Newcomer of the Year and first team freshman All-America Steve Davis. In 2005, Minnesota defeated Michigan for the first time in 19 years to recapture the Little Brown Jug given to the winner of the 100 plus year-old rivalry. During the 2006 season the defensive line accounted for 20.5 sacks. The Minnesota defense led the Big 10 in turnover margin, red zone defense, and turnovers gained. Another pupil of Bailey, defensive end William VanDeSteeg, led the Big 10 in sacks during to 2006 season (conference games). While at Minnesota, the Golden Gophers participated in the 2005 Music City Bowl, and the 2006 Insight Bowl.
On February 17, 2007, Bailey was named head football coach at Howard University. While leading the Bison, he produced four first team All-America players (Sheridan Broadcast Network), and eleven All-Conference (Mid-Eastern Athletic Conference) players. Bailey resigned from his position on December 6, 2010.
Carey Bailey accepted the position of defensive line coach at Lamar University on February 16, 2012. In 2012, the Lamar Defense produced its best performance since joining the Southland Conference and two of Bailey's pupils garnered All-Conference recognition. In 2013, the Lamar Defense recorded its highest sack total in school history. Defensive End Jesse Dickson became Lamar's first All-America (TSN) and first two time All-Conference Defensive Lineman in the modern era. The 2013 Conference Defensive Player of the Year (College Sports Madness) was the conference leader in tackles for loss. Dickson led the team in tackles, tackles for loss and sacks under Bailey's tutelage. Jesse Dickson was the only defensive lineman to finish ranked in the top 10 for tackles in the Southland Conference.
In 2013, Coach Bailey was given charge of the defensive kicking teams. Bailey fielded a punt return unit that finished the 2013 season ranked #2 nationally (NCAA-FCS) and led the Southland conference in punt returns. The #2 NCAA ranking was an improvement of 88 spots from the previous year. Punt Returner Kevin Johnson was named National Punt Returner of the Year (CFPA) and earned All-Conference honors. On February 4, 2014 Bailey was promoted to Assistant Head Coach.
Lamar finished the 2014 football season with an 8-4 record and a #3 ranking in the Southland Conference. The 8 win mark was the most wins since the bringing the program back in 2010, and tied a school record for most wins in program history. Coach Bailey guided a defensive front in which the entire starting unit received all-conference recognition, highlighted by the second team selection of sophomore Omar Tebo. Coach Bailey helped the Lamar Defense set a school record for sacks, lead the Southland Conference in fumbles recovered and finish 11th nationally in turnovers gained.
In 2015 Carey Bailey coached a defenese that led the Southland conference in Turnovers Gained and finished 3rd in Tackles for loss. Coach Bailey tutored yet another All-Conference performer for the Cardinals in Larance Hale. Hale proved to be the most productive defensive lineman in the Southland conference. The First Team All-Conference selection was the 2nd leading tackler for the Cardinals and the team leader in forced fumbles, while finishing first among all Southland conference defensive linemen in Sacks (7.5), Tackles (86) and Tackles for loss (21.5). Hale also finished 9th in tackles and was 5th in forced fumbled among all defensive players in the Southland Conference.
In June 2012, Carey Bailey was selected to participate in the BIll Walsh Fellowship program with The Atlanta Falcons. Coach Bailey worked with the Linebackers during the 2012 pre-season training camp.
In May 2015, Carey Bailey was selected once again to participate in the Bill Walsh Fellowship program as a coaching intern, this time with the New York Giants. Coach Bailey worked with the Linebackers and coached through the first preseason game against the Cincinnati Bengals.
On January 18, 2016 Coach Bailey was named Defensive Line Coach at the University of Tennessee at Chattanooga. During the 2016 season the Mocs defensive line proved to be one of the best in all of FCS. The UTC defense led the Southern Conference and set a school record for team sacks with 38 of which 30 came from the defensive line. Defensive ends Keonta Davis and Vantrell McMillan both earned first team all Southern conference recognition. Davis was also named First Team All-American and the Southern Conference Defensive Player of the Year. Hero sports named Davis the top Defensive End in FCS and the Top NFL prospect at his position. UTC finished the 2016 campaign ranked 10th in the country with a 9-4 record, while finishing 6th in total defense (up 27 spots from 2015), 9th in scoring defense (up 30 spots from 2015) and 12th in sacks (up 11 spots from 2015).
On December 18, 2016 Coach Bailey was named Defensive Line Coach after former Chattanooga Head Coach Russ Huesman was named Head Football Coach at the University of Richmond.
On September 25, 2009, Carey Bailey was inducted into the Morgantown High School Athletic Hall of Fame.
Over the span of his coaching career 16 of his pupils have played professional football. Coach Bailey has coached 7 All-America, 28 All-Conference players and 3 Conference Player of The Year honorees.