Bob Kaiser attended Oak Hills from 1964 - 1967. He was a member of the baseball and basketball team. While at Oak Hills Bob was an all-conference, all-city and all district performers in both sports. He played at Oak Hills for Hall of Fame Coach Steve Moore. In 1968 Bob was a third round draft pick of the Cleveland Indians. Bob played professionally for the Cleveland Indians, Detroit Tigers and Pittsburgh Pirate organizations. The highlight of his career was in 1972 when he beat the Cincinnati Reds while pitching for the Indians. After his professional baseball career, Bob went on to coach in college, high school and many youth teams. 

Hep Cronin was the head basketball coach at Oak Hills High School from 1981 - 1986. He led the Highlanders to an amazing 102-24 record in those six seasons. He coached 3 league championship teams, was a district champion. In 1983 Hep lead the Highlanders to an undefeated regular season. Eight of Coach Cronin's former players went on to play Division I corner and enjoys post season success. 

Kathy Rembold Garry is a 1985 graduate of Oak Hills. During her career at Oak Hills she was a three year varsity letter winner in tennis and a three year varsity letter winner in basketball. On the basketball court, Kathy was named all-league and all-city. She was a two year team captain and led her team to two conference championships. As a tennis player, Kathy was a three time conference champion. She won the sectional and district titles both as a singles player and as a doubles player. As a junior, she was named first team all conference, all district and selected first team all-city by both the Cincinnati Enquirer and the Cincinnati Post. In her senior season, she again was named first team all-conference, all districts and all cities. Kathy is the only female tennis player in Oak Hills history to qualify for the state finals. After high school, Kathy graduated from Miami University. The Rembold family has a long history with Oak Hills. Kathy's grandfather, Gilmore Year out, helped name Oak Hills High School. Gilmore Year out is included in the prestigious Oak Hills Local School District Wall of Honor.