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. 

Chuck was a member of the class of 1968, and was a varsity athlete in Baseball, Basketball, and Football. From 1967-1968, he was All-League and All-City in all three sports, which included leading Oak Hills to league titles in Baseball and Basketball. He was the leading scorer for the Oak Hills Football team, as well as led the city in his senior year in scoring. Chuck also led the Oak Hills Baseball team with a .330 batting average, and was 7-0 in starts during his senior year. He accepted a full athletic scholarship to Eastern Kentucky University, where he was awarded Newcomer of the Year before suffering a career ending knee injury in his final game against University of Kentucky. 

David Soult, class of 1989, was a 3 sport Varsity Athlete, competing for the Varsity Football, Basketball and Baseball teams. As a football player, he earned 3 Varsity Letters, and earned multiple awards, including 2nd Team All-League his Junior year and 1st Team All-League and 2nd Team All-City his Senior year. He still holds multiple football records at Oak Hills, including Touchdowns for a career (35) and tied for 1st in Touchdowns in a single season (23). As a member of the Varsity Baseball Team, Soult earned 3 Varsity Letters and earned many awards during his playing career at Oak Hills. He earned 1st Team All-League all 3 years he was a member of the Varsity team, and 1st Team All-City his Junior and Senior Seasons. After high school, he accepted a Baseball Scholarship to the University of Kansas. 

Grant Griesser is 1985 graduate; Grant was a three sport standout for the Highlanders. As a member of the football team he earned all-league honors during his junior and senior seasons. On the basketball court he was a member of the 1984 squad that posted a perfect 20-0 record on their way to a conference and city championship. His senior basketball season, Grant lead to the team to a conference and district championship. While his success in football and basketball are impressive, his love and passion was baseball. During his two seasons as the starting catcher for Oak Hills, he led the team to two conference championships and a record of 49-3. During his senior season, Grant was named first team all-conference in three sports. His combined record in games started for Oak Hills is an amazing 92-24, including 116 starts. Grant was awarded a baseball scholarship to Miami University where he went on be a four year starting catcher and earn All Mid-American Conference honors for two years. Following his college career, Grant signed to play with the Kansas City Royals organization. He played minor league baseball for six years. After his playing days were complete, he went on to earn his undergraduate and master's degree. 

Jason Martin was a member of the Oak Hills Graduating Class of 1998, in which he played varsity Football, Basketball, and Baseball. He earned the Senior Athlete Award and the Archie Griffin Award for Leadership in 1998. Martin had sustained success for the Highlander Baseball team, being a starter on 2 league championship teams. He currently holds the 2nd place records for single season batting average (.519) and Career average (.456). His senior season, he was named to the Mizuno All-Ohio All Star Team, All-City 1st Team, and Conference Co-Player of the Year. That season, he led the team in Hits, RBI's, Triples, and HR's. 

Jeff Flynn, also known as “Fly”, played basketball at Oak Hills under coach Hep Cronin, from 1982-1985.  His senior year he led the Highlanders to a perfect 20-0 record and was selected 1st Team All City and 3rd Team All State.  Jeff went on to play for Tony Yates at the University of Cincinnati from 1985-1989.   Jeff currently works for the Armor Group as a project manager.  He and his wife Patricia have two children, Kevin and Kierstin.

Jeff Weddle is a 1971 graduate who lettered in basketball and baseball. Jeff earned six varsity letters as a student athlete at Oak Hills High School. In basketball, he led Oak Hills to a 56-5 record over his three varsity seasons. During that time Oak Hills was three time league champion, and in 1971 they were City Champions. Jeff was named all-league and all city in basketball for two seasons. His senior season, while serving as one of the co-captains, Jeff led the Highlanders to an 18-0 regular season record. Jeff was the ultimate team player leading the team in assists. In 1971, Jeff represented Oak Hills in the first ever East -West All Star All City game. On the 1971 baseball team, Jeff had an earned run average of 0.26, and a batting average over three-hundred. His senior year, Jeff was awarded the Outstanding Senior Athlete Award. After his career at Oak Hills, Jeff went on to play basketball at Valparaiso University. 

Jessica was a 4 year varsity basketball letterwinner while at Oak Hills, where she was All-GMC and All-City all 4 years. She received district player of the year in the 2006-2007 season, as well as Honorable Mention All-State in the 2005-2006 season. At the conclusion of her 4 year varsity stint, she concluded with back to back All-State nominations from 2006-2008, and ended as the Oak Hills career leader in points. She went on to accept an athletic scholarship to continue her playing career at the Marquette University, where she earned Big East All-Freshman Team Honors. She then transferred to Xavier University where she finished her playing career, where she earned Atlantic 10 All-Academic Team, and became a part of the Xavier 1000 point club. 

Joe Dooley is 1980 graduate and was a standout football, track and basketball student athlete at Oak Hills earning All-League honors in all three sports. As a member of the Oak Hills track team he was crowned League Champion in the shot put and discus in 1979 and in discus in 1980, qualifying for regionals both seasons. Joe is most widely known at Oak Hills as a dominant football player. As a senior Joe earned All-State honors and earned a full football scholarship to the Ohio State University. While a member of the Buckeyes football program, Joe was a three year letter winner. His senior season as the starting center, Joe lead the Buckeyes to a 9-3 record and a Fiesta Bowl Championship under head coach Earl Bruce. In 1984 Joe was the second Oak Hills Highlander to be drafted by the National Football League when he was taken by the Los Angeles Rams in the 10th round. 

Joe Rothwell is 1975 graduate, and was a three sport standout for the Highlanders. He was a three year varsity letter winner in football, helping the team to the 1974 league championship. He also lettered in basketball. His passion was baseball where he earned three varsity letters. During his baseball career at Oak Hills, Joe was named all-conference and all city three times. In 1974, he led the Highlanders to a baseball conference championship. While Joe was offered several football scholarships, he decided to accept a baseball scholarship to Southern Illinois University, a Perennial National contender in the mid to late 1970's. After his freshman season at SIU, Joe was selected in the 12th round of the Major League draft by the Kansas City Royals. In 1975 Joe was selected to the All-Rookie team while playing for the Sarasota Royals. After two seasons in the Royals organization he was traded to the Detroit Tigers where he played for an additional three seasons. While with the Detroit Tigers he was selected to the Appalachian League All Star Team in 1978. After his playing career was complete, Joe completed his college education at the University of Cincinnati under the Professional Baseball Scholarship Plan. 

Larry Land is 1990 graduate, and was also a standout basketball player for the Highlanders. He was a three time all conference performers and was named Conference Player of the Year in 1990. During his three year high school career, the Highlanders captured a District Championship and advanced to the elite eight in the State of Ohio. Because of his standout career at Oak Hills, Larry was awarded a full scholarship to the University of St. Francis. After four years at USF he finished as the career leader in 3-point field goals made and games played in school history. He was also in the top five for career 3-point percent, career scoring average, career FT's attempted and made and career scoring. In 2007, Larry was inducted into the University of St. Francis Athletic Hall of Fame, making him the first Oak Hills basketball player to be inducted into their collegiate Athletic Hall of Fame. 

Todd Dietrich was a member of the graduating class of 1977 at Oak Hills, and played Varsity Basketball for the Highlanders. During his time at Oak Hills, He was named a 3 time All-League and All-City player in 1975-1977, was an All-State performer in 1976 (1st Team) and 1977 (2nd Team). He was named a Street and Smith Honorable Mention All-American in 1977, and was named the Ohio Player of the Year that same year. Following his graduation from Oak Hills, Dietrich accepted a Full Basketball Athletic Scholarship to Western Michigan University. 

Tom Price was a graduate of Oak Hills in the class of 1979 has earned the Meritorious Service Award. During his time at Oak Hills, he was a member of 3 Varsity Sports, which were Basketball, Soccer and Tennis. Since 1983, Price has been involved with Oak Hills Junior Pro, now OHYA as a Coach, Board and Committee Member, Treasurer, Program Coordinator, and Referee Coordinator. He has also been an Oak Hills Booster Board Member for 7 years. He was also the school Basketball coach at Delhi, Bridgetown, and Oak Hills (volunteer). He also helped by operating the scoreboard at football and basketball games, chains for the football games, and kept the scorebook for both Men's and Women's Basketball games. He also spends free time volunteering in capacities such as Split the Pot vendor at athletic events and the Booster Athletic Stag.