| Jini and Jim | Accommodation and Food Services | $48,569 | $48,895 | 15 | <$5M |  AI Deep Dive |
| Pflughoeft Pederson & Johnsrud LLP | Professional, Scientific, and Technical Services | $48,060 | $48,473 | 3 | <$5M | AI Deep Dive |
| Pflughoeft, Pederson & Johnsrud, LLP | Professional, Scientific, and Technical Services | $48,000 | $48,328 | 3 | <$5M | AI Deep Dive |
| Mugby Junction INC | Accommodation and Food Services | $47,500 | $42,253 | 10 | <$5M | AI Deep Dive |
| Autowerks Tire & Tune | Other Services (except Public Administration) | $47,297 | $47,490 | 5 | <$5M | AI Deep Dive |
| Todds Refrigeration LLC | Construction | $46,500 | $46,844 | 4 | <$5M | AI Deep Dive |
| Winona County Historical Society | Arts, Entertainment, and Recreation | $46,346 | $46,852 | 8 | N/A | AI Deep Dive |
| Island City Brewing Company | Manufacturing | $46,270 | $46,864 | 10 | <$5M | AI Deep Dive |
| Island City Brewing LLC | Manufacturing | $46,200 | $46,718 | 14 | <$5M | AI Deep Dive |
| Lc Winona LLC | Accommodation and Food Services | $45,909 | $46,160 | 20 | <$5M | AI Deep Dive |
| Todd Funk | Health Care and Social Assistance | $45,347 | $45,675 | 1 | <$5M | AI Deep Dive |
| Bluff City Properties, LLC | Professional, Scientific, and Technical Services | $45,000 | $45,365 | 4 | <$5M | AI Deep Dive |
| St Mary's Cemetery of Winona Minnesota | Other Services (except Public Administration) | $44,882 | $45,134 | 5 | N/A | AI Deep Dive |
| Independence Ready Mixed Concrete Co., INC | Construction | $44,802 | $45,086 | 2 | <$5M | AI Deep Dive |
| Winona Marina LLC | Arts, Entertainment, and Recreation | $44,730 | $45,054 | 12 | <$5M | AI Deep Dive |
| R&r Machining Company | Manufacturing | $44,600 | $44,866 | 4 | <$5M | AI Deep Dive |
| Winona County Historical Society | Arts, Entertainment, and Recreation | $43,900 | $44,161 | 10 | N/A | AI Deep Dive |
| R & R Machining Company | Manufacturing | $43,715 | $43,921 | 4 | <$5M | AI Deep Dive |
| Hope Lutheran High School | Educational Services | $43,200 | $43,643 | 5 | N/A | AI Deep Dive |
| Bluff City Properties LLC | Real Estate and Rental and Leasing | $43,097 | $43,417 | 4 | <$5M | AI Deep Dive |
| Winona Convention & Visitors Bureau | Administrative and Support and Waste Management | $42,748 | $42,973 | 7 | <$5M | AI Deep Dive |
| Cada Concrete Plus, LLC | Construction | $42,500 | $42,249 | 8 | <$5M | AI Deep Dive |
| Steve Young Agency, Inc. | Finance and Insurance | $42,500 | $42,725 | 5 | <$5M | AI Deep Dive |
| Hv Management Co INC | Real Estate and Rental and Leasing | $41,900 | $42,392 | 4 | <$5M | AI Deep Dive |
| Advocacy Center of Winona | Health Care and Social Assistance | $41,900 | $42,149 | 5 | N/A | AI Deep Dive |