Captain Cliff Mathews

Captain Cliff Matthews' retirement marks the conclusion of one of the most distinguished careers in the history of the Upland Police Department. After 35 years of dedicated service to the City of Upland, Captain Matthews retires as the longest-serving police officer in the department's 120-year history, leaving behind an extraordinary legacy of leadership, innovation, and unwavering commitment to public safety.

Captain Matthews began his law enforcement career with the UC Riverside Police Department in 1988 before joining the Upland Police Department in 1991. From the very beginning, he demonstrated a passion for service and an exceptional commitment to professional excellence. Throughout his career, he rose through every major rank within the department—serving as police officer, detective, sergeant, lieutenant, captain, and ultimately as Interim Chief of Police in 2017. Few individuals have had the opportunity to lead from every level of an organization, and even fewer have done so with the respect and admiration Captain Matthews earned throughout his career.

As a detective, Captain Matthews became a pioneer in technology-driven law enforcement. He established the department's High-Tech Crime Unit and became one of the first computer forensic investigators in San Bernardino County, helping position the Upland Police Department at the forefront of digital investigations during a time when computer crime was still an emerging field.

Over the course of his career, Captain Matthews provided leadership over nearly every major function of the department, including investigations, patrol operations, training, crime prevention, code enforcement, communications and dispatch, records, and fiscal services. His breadth of knowledge and institutional experience made him an invaluable leader whose guidance helped shape the department for generations of officers.

His dedication to excellence was recognized throughout his career with numerous honors, including Officer of the Year, a Life Saving Award, the Excellence Award, multiple Officer of the Month recognitions, and a Community Service Award from the Chaffey Joint Union High School District. These awards reflect not only his professional accomplishments but also the compassion, integrity, and service that defined his career.

Captain Matthews also believed that learning never ends. While serving the citizens of Upland, he earned an Associate Degree, a Bachelor of Science in Public Administration with magna cum laude honors, and a Master of Science in Emergency Services Administration—demonstrating a lifelong commitment to professional growth and leadership.

Perhaps Captain Matthews' greatest contribution cannot be measured by awards or titles, but by the people he influenced. He mentored countless officers and supervisors throughout his career, helping develop future leaders within the department. His wisdom, steady leadership, and trusted counsel have left a lasting impact on the Upland Police Department, with many leaders—including the current Chief of Police—crediting Captain Matthews for shaping their own leadership philosophies and careers.

Long before his law enforcement career began, Captain Matthews demonstrated his commitment to service by earning the rank of Eagle Scout, a distinction that reflects the values of integrity, leadership, and dedication that would come to define his life.

As Captain Cliff Matthews retires on June 30, 2026, he leaves behind more than 35 years of faithful service—he leaves behind a stronger police department, a safer community, and a legacy that will continue to influence the City of Upland for years to come. His career stands as an enduring example of professionalism, innovation, humility, and selfless public service.

On behalf of the City Council and the residents of Upland, we extend our deepest gratitude to Captain Cliff Matthews for his remarkable career and wish him and his family many years of health, happiness, and a well-deserved retirement.

Disclaimer: The Upland Update is an independent community resource and is not affiliated with the City of Upland. This is my personal initiative to keep residents and businesses informed about key issues, city developments, and community events that impact our daily lives. My goal is to ensure you have clear, transparent, and timely information to stay engaged and involved in shaping Upland’s future.

James Breitling

(909) 342-2523

info@theuplandupdate.com

© 2025. All rights reserved.