In the 1980s, the Kansas City born guitarist began playing in groups lead by some of the city's world renowned recording artists beginning with the late trumpeter Carmel Jones, who had recorded with Horace Silver. Matthews also played and recorded with violinist Claude 'Fiddler' Williams, who was Count Basie's first guitarist before Freddie Green. In 1989, Matthews had the opportunity to play a concert with pianist/vocalist Jay McShann's big band, and then also perform with McShann's quintet in 2003. Additionally, Matthews played in the quartet and trio of GRAMMY® winning pianist and composer, Dr. Ronnell Bright - who after many years of accompanying and recording with vocalist like Sarah Vaughan, Ella Fitzgerald, Lena Horne, Nancy Wilson, Carmen McRae and serving as musical director for the Flip Wilson and Carol Burnett shows; had decided to make Kansas City his home.

And, begining in the early 1980s he was performing in various configurations with saxophonist Ahmad Alaadeen - recording on Alaadeen's, 'Blues for RC and Josephine, Too (ASR1001) release. For more than twenty years Matthews has been performing with another longtime mentor, pianist/vocalist, Luqman Hamza; whom he has recorded two projects with: 'When a Smile Overtakes a Frown' and 'The Clear Sounds Of Jazz'. Matthews has also had the opportunity to play one-nighters with a variety of artists coming through Kansas City such as Charles Earland, Freda Payne, Arthur Prysock, Jimmy Witherspoon, Carmen Bradford, Kevin Mahogany and Bobby Watson. Matthews has also played guitar and banjo for the ground-breaking opera: "Treminisha", written by Scott Joplin.

In 1996 Matthews joined the world-famous Count Basie Orchestra, then under the direction of trombonist Grover Mitchell, to fill the coveted chair of the late Freddie Green. Green had been the guitarist in the Count Basie Orchestra for over fifty years. Since joining the Count Basie Orchestra, Matthews has played on numerous recordings, including two "GRAMMY® Winning" releases. He has performed at venues and events that include the Royal Palace in Bangkok, Thailand and President William J. Clinton's Second Inaugural. So far during his tenure with the Count Basie Orchestra, Matthews has performed with a literal who's who of artists, including: Joe Williams, Frank Foster, Benny Carter, Milt Jackson, George Benson, Kenny Burrell, Nancy Wilson, Patti Austin, Marlena Shaw, Carmen Bradford, Tony Bennett, Dianne Reeves, Jimmy Cobb, Hank Jones and Nnenna Freelon. Today, Matthews’s activities primarily continue to revolve around his performing and touring schedules with the Basie Orchestra.

Matthews is currently completing a brand new CD project that will be commercially released and distributed globally as part of the 'ASR RECORDS front catalogue of titles. His debut recording, ‘Will Matthews Solo’, was initially released in November of 2000, and will now be reissued and distributed by the label as well.