| $150,000–350,000 | THE TOWNSEND COMPANIES INC | CHESAPEAKE, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $150,000–350,000 | THE WILD WING CANTINA INC | CHESAPEAKE, VA | Atlantic Union Bank |
| $150,000–350,000 | THERMAL SPRAY SOLUTIONS, INC | CHESAPEAKE, VA | Atlantic Union Bank |
| $150,000–350,000 | TIDEWATER AUTO PAINTING, INC. | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | TIDEWATER COMMERCIAL CEILINGS & WALLS, INC | CHESAPEAKE, VA | Atlantic Union Bank |
| $350,000–1 million | TIDEWATER EMERGENCY MEDICAL CARE LTD | CHESAPEAKE, VA | Towne Bank |
| $2–5 million | TIDEWATER FIBRE CORP | CHESAPEAKE, VA | Towne Bank |
| $350,000–1 million | TIDEWATER GASTROENTEROLOGY PLLC | CHESAPEAKE, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $350,000–1 million | TIDEWATER HEALTHCARE SERVICES, INC | CHESAPEAKE, VA | Blue Ridge Bank, National Association |
| $350,000–1 million | TIDEWATER HOME FUNDING, LLC | CHESAPEAKE, VA | Atlantic Union Bank |
| $350,000–1 million | TIDEWATER INTERIOR WALL AND CEILING, INC. | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | TIDEWATER LANDWORKS, INC. | CHESAPEAKE, VA | Atlantic Union Bank |
| $350,000–1 million | TIDEWATER MACK INC. | CHESAPEAKE, VA | Atlantic Union Bank |
| $150,000–350,000 | TIDEWATER WINGS INC | CHESAPEAKE, VA | Fulton Bank, National Association |
| $350,000–1 million | TIPS EAST LLC | CHESAPEAKE, VA | FirstBank |
| $150,000–350,000 | TITAN TALENT DEVELOPMENT LLC | CHESAPEAKE, VA | PNC Bank, National Association |
| $150,000–350,000 | TITLEQUEST OF HAMPTON ROADS, LLC | CHESAPEAKE, VA | Towne Bank |
| $350,000–1 million | TRADE TEAM USA, LLC | CHESAPEAKE, VA | Towne Bank |
| $2–5 million | TRADE TEAM, LLC | CHESAPEAKE, VA | Towne Bank |
| $350,000–1 million | TRI-STAR ELECTRIC, INC. | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | TRINITY SALON INC | CHESAPEAKE, VA | Bank of America, National Association |
| $150,000–350,000 | TSO ARMOR AND TRAINING INC. | CHESAPEAKE, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $350,000–1 million | VANWIN COATINGS OF VA, LLC | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | VENUWORKS OF CHESAPEAKE, L.L.C. | CHESAPEAKE, VA | Availa Bank |
| $1–2 million | VICO CONSTRUCTION CORPORATION | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | VIRGINIA EQUIPMENT RENTAL, INC | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | VIRGINIA FLOORCRAFTERS, INC. | CHESAPEAKE, VA | Farmers Bank |
| $150,000–350,000 | VIRGINIA LANDSCAPE MANAGEMENT INC | CHESAPEAKE, VA | Wells Fargo Bank, National Association |
| $150,000–350,000 | VIRGINIA NEUROLOGY AND SLEEP CENTER | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | VIRGINIA RV SOLUTIONS, INC. | CHESAPEAKE, VA | Towne Bank |
| $350,000–1 million | VIRGINIA TRAILER SERVICES INC | CHESAPEAKE, VA | Bank of America, National Association |
| $150,000–350,000 | W. TODD BIVINS DDS MS PC | CHESAPEAKE, VA | Truist Bank d/b/a Branch Banking & Trust Co |
| $350,000–1 million | WATERSHED SECURITY LLC | CHESAPEAKE, VA | PNC Bank, National Association |
| $150,000–350,000 | WATERWAY PLUMBING INC | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | WB&E CONSTRUCTION, INC. | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | WEATHER MAKERS, INC. | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | WEB TEKS, INC. | CHESAPEAKE, VA | Towne Bank |
| $350,000–1 million | WEST SERVICE CENTER, INC. | CHESAPEAKE, VA | Towne Bank |
| $150,000–350,000 | WESTVIEW FINANCIAL SERVICES VA LLC | CHESAPEAKE, VA | Atlantic Union Bank |
| $350,000–1 million | WHITE'S NURSERY AND GREENHOUSES, INC. | CHESAPEAKE, VA | Celtic Bank Corporation |
| $150,000–350,000 | WHOOPING CRANE, INC. | CHESAPEAKE, VA | Towne Bank |
| $350,000–1 million | WINKE ORTHOPEDIC PAIN MANAGEMENT CENTER PLC | CHESAPEAKE, VA | Towne Bank |
| $350,000–1 million | ZERO POINT INC. | CHESAPEAKE, VA | Towne Bank |