Dick Birmingham was the first coach of Hillcrest Baseball. He started at there in 1960 and quickly turned Hillcrest into a state powerhouse finishing ranked in the top three in American Legion in '62, '63, '64, and '67. In 1970 Birmingham finally broke through and won the American Legion State Championship finishing with 48 wins. The next year Hillcrest repeated as state champions becoming one of only four schools to win back to back State Championships since the Legion program went statewide. Dick led the Legion team to one more state title in 1976 before stepping away from the summer program. But he wasn't done, in 1979 he coached the Hillcrest school ball team to their first state title in its 20th year. Birmingham retired from Hillcrest after the 1984 season but not before he amassed 887 career wins between school ball and legion more than any other coach. He also won 15 conference titles, 13 school ball districts, 9 legion districts, and 4 total State Championships. In his 25 years at Hillcrest Birmingham coached 20 players onto play pro baseball, including four off the 1971 team and six off the 1966 team (a national record for over 30 years). Because of all he did for the Hillcrest program the school named the baseball field Dick Birmingham Field. After his high school coaching ended Dick started Dick Birmingham Sports and puts on baseball camps all over the U.S. for all ages and also runs clinics for coaching. In 1990, he was the first member inducted into the Missouri High School Baseball Coaches Hall of Fame and was later inducted to the Missouri Sports Hall of Fame in 2002.

Dave Davis succeeded Dick Birmingham as head coach of Hillcrest High School before the 1985 season. Davis was a former stand-out player for Central High School in Springfield and was picked to take over as only the second coach Hillcrest had ever had. Taking over for a local legend like Birmingham was no easy task, but Davis more than completed the task. In his 10 years as head coach he won 144 games for a .673 inning percentage and led Hillcrest to a legion and school ball State Championship in 1987 and 1988, respectively. Davis also led his school ball teams to 4 conference titles and 3 district titles in his tenure. Since leaving coaching at Hillcrest he has continued teaching Broadcast Journalism there. After starting his media program in 1989, Davis has built a nationally renown news program called HTV Magazine. In 17 years HTV has won numerous awards including six broadcast Pacemaker awards, three Robert F. Kennedy Student Journalism awards, and it was Channel One's #1 Newscast in 1995, 1997 and 1999.

Byron Hagler became Hillcrest's third head coach before the 1995 season after 15 years at Licking High School where he amassed 348 wins and 2 State Championships. He did not stop winning once he arrived at Hillcrest. Hagler started a new beginning to the old tradition with 9 district titles between school ball and legion in his 12 years. In 2002, he led the legion team to its first State Championship in over 15 years. After 2006 Hagler retired from coaching high school baseball but not before he finished with the highest winning percentage of any other coach in the history of Hillcrest at .695. He finished at Hillcrest with 490 combined wins, 7 conference championships, 5 school ball and 4 legion district titles, 2 Final Fours, and 1 State Championship. Hagler was also inducted to the Missouri High School Baseball Coaches Association Hall of Fame in 2000 and coached 2 players from Hillcrest that went on to play pro baseball. Currently, Coach Hagler is the pitching coach for the Drury University baseball team as they begin thier first season in 2007.

Ryan Schaffitzel began his first season as head school ball coach in 2007 but has held the reigns of the legion program since 2003. Schaffitzel wasted no time in making his own tradition by winning the district in his first year finishing with 45 wins, most ever by rookie head coach at Hillcrest. Overall, Schaffitzel has won two district titles in his five years and amassed 149 wins. He started coaching in the program in 1992 leading the rookie legion team just one year after he graduated from Hillcrest. His 17 years of service toward the program made him the overwhelming choice to take over for Byron Hagler as only Hillcrest's fourth head coach in 47 years.