- Advanced Mediator Training–USA&M 2022
- Civil Mediation Training, University of Missouri-Columbia, 2022
- J.D. University of Missouri-Columbia, 1982
- Northeast Missouri State University, n/k/a Truman State University, B.S.E. History, Magna Cum Laude, 1978
Judge Cunningham served over 31 years as a judge of the St. Charles County Circuit Court. He served as an associate circuit court judge for 16 years and 15 years as a circuit court judge. He served as Presiding Judge of the Circuit during the years of 2009 and 2010. In 2000, Judge Cunningham was appointed to be the first Drug Court Judge in St. Charles County. He also served as Probate Judge of the Circuit for 7 years. Judge Cunningham presided over thousands of civil motions and bench trials, both civil and criminal. During his years as a judge, he also participated in hundreds of settlement conferences. In 2016, Judge Cunningham was appointed to the Missouri Circuit Court Budget Committee and served on that Committee until his retirement from the bench in 2022. In 1996, Judge Cunningham was honored to serve as the President of the St. Charles County Bar Association. Prior to being elected judge, Judge Cunningham practiced law in St. Charles, MO in a general civil practice.
- Missouri Bar
- St. Charles County Bar Association