Paul Woolley was a graduate of Montevallo High School and Howard College, now Samford. Woolley served as an assistant coach at Tuscaloosa County for two seasons before embarking upon his head coaching career.

Woolleys first job as a head football coach came in 1966 at Thompson High School. He remained at the school for two seasons with a 7-13 record. His next stop was at Hokes Bluff in 1968-69 where his teams went an unimpressive 1-19.

Woolley landed at Montevallo High School for one year in 1972 and claimed a 3-6-1 slate. Things began to turn around for Coach Woolley in 1974 when he took over the football program at Handley.

His 1977 team finished the season with a 12-2 record and reached the State Championship game before falling short of a title. Four of his six teams won an area title and made the playoffs.

In 1980, Woolley accepted the head football job at Brantley. Over the next eight years his Bulldogs went 60-31-1. His 1983 team reached the state finals and the 1985 squad completed the regular season undefeated before falling in the second round of the playoffs.

The Bulldogs won four area titles and qualified for the playoffs five times during his tenure at the school.

Coach Woolley spent one season at Monroe County High School before moving on to Opp in 1989. His six Bobcat teams combined for a 40-23 record with four more playoff spots and four area titles.

When the football season opened in 1995, Coach Woolley was found at Fort Dale Academy. His four teams at Fort Dale went 27-17 and made the playoffs three times. He stepped down following the 1998 season with the Bobcats.

The Andalusia Bulldogs had finished the 1998 season with a 2-8 record and looked to Coach Woolley for direction in a once storied program that had a great run some years prior under Don Sharpe.

The Bulldogs had not reached the playoffs since 1986 when Woolley arrived for the 1999 season. In four seasons Coach Woolley did take the Bulldogs back to the playoffs with a couple of appearances but not exactly to the by-gone glory days. His four teams went 19-23.

His over football record is 199-168-2 in 34 seasons as a head football coach in Alabama. His teams went 15-18 in playoff games and won nine area and region titles.

Woolley served two terms as the President of the AHSAA Coaches Association. He was the coach of South team in the North-South All-Star game in Tuscaloosa and was named Coach of the Year a total of thirteen times.

He was inducted into the Alabama High School Athletic Associations Hall of Fame in 1998.