Beginning his career at DIII Johnson & Wales University, Dave Matthews spent two summers playing in the Futures Collegiate League with the Torrington Titans and Pittsfield Suns. He then transferred to DI Central Connecticut State and had to sit out of the 2018 season.  

In 2019, he was named an All-NEC 2nd-Team Member where he led the Blue Devils in home runs, runs scored, walks and RBI. From there, he went to the New England Collegiate League’s Keene Swampbats for 30 games of competition. His 2020 CCSU campaign was cut short after 12 games, but he managed to play summer ball for the Westfield Starfires. 

After one final season with CCSU in 2021, he began his pro career with 30 games for the Joliet Slammers in the Frontier League where he launched his first pro home run. He played the 2022 season with Joliet as well where he hit two more long balls. 

Matthews moved out west for the 2023 season to play for the Northern Colorado Owlz of the Pioneer League where his average spiked to .325 in the Rocky Mountains including a power surge to 22 home runs. In 2024, he played an additional 88 games with the Owlz, totaling another 19 home runs on a .354 average. 

Now, he begins a stop in his third professional league with the Dockhounds in 2025.