| Cada Concrete Plus LLC | Construction | $24,046 | $24,242 | 4 | <$5M | AI Deep Dive |
| Laverne Frederick Thill | Agriculture, Forestry, Fishing and Hunting | $24,015 | $24,126 | 2 | <$5M | AI Deep Dive |
| D&l Johnson Dairy Farm LLC | Agriculture, Forestry, Fishing and Hunting | $24,000 | $24,231 | 3 | <$5M | AI Deep Dive |
| Luxury Nails & Spa LLC | Other Services (except Public Administration) | $23,975 | $24,084 | 5 | <$5M | AI Deep Dive |
| Sandstone Sales | Wholesale Trade | $23,957 | $24,074 | 2 | <$5M | AI Deep Dive |
| Scott Evans Agency, Inc. | Finance and Insurance | $23,700 | $23,944 | 1 | <$5M | AI Deep Dive |
| Valley View Car Wash LLC | Other Services (except Public Administration) | $23,655 | $23,719 | 2 | <$5M | AI Deep Dive |
| Lutheran Campus Ministry of Winona INC | Other Services (except Public Administration) | $23,655 | $23,771 | 8 | N/A | AI Deep Dive |
| Faith Lutheran Church | Other Services (except Public Administration) | $23,452 | $23,536 | 5 | N/A | AI Deep Dive |
| Wicka Concrete Construction LLC | Construction | $23,435 | $23,575 | 4 | <$5M | AI Deep Dive |
| John Stevens Construction LLC | Construction | $23,395 | $23,448 | 2 | <$5M | AI Deep Dive |
| Market Street Tap, LLC | Accommodation and Food Services | $23,300 | $23,458 | 16 | <$5M | AI Deep Dive |
| Rkd Ready Mix, Inc. | Manufacturing | $23,000 | $23,146 | 1 | <$5M | AI Deep Dive |
| Geran Inc. | Construction | $23,000 | $23,144 | 2 | <$5M | AI Deep Dive |
| Wesley United Methodist Church of Winona | Other Services (except Public Administration) | $22,795 | $22,903 | 6 | N/A | AI Deep Dive |
| Lutheran Campus Ministry of Winona, Inc. | Other Services (except Public Administration) | $22,700 | $22,844 | 8 | N/A | AI Deep Dive |
| Great Hunan | Accommodation and Food Services | $22,635 | $22,924 | 7 | <$5M | AI Deep Dive |
| Blooming Grounds Express LLC | Accommodation and Food Services | $22,600 | $22,760 | 8 | <$5M | AI Deep Dive |
| Larson Building and Remodeling, LLC | Construction | $22,600 | $22,732 | 3 | <$5M | AI Deep Dive |
| Styx Concrete LLC | Construction | $22,597 | $22,756 | 4 | <$5M | AI Deep Dive |
| Chad Brink | Accommodation and Food Services | $22,400 | $22,618 | 15 | <$5M | AI Deep Dive |
| Wenonah Property Group INC | Accommodation and Food Services | $22,253 | $22,322 | 11 | <$5M | AI Deep Dive |
| Jay & Dee's Special T's LLC | Professional, Scientific, and Technical Services | $21,972 | $22,074 | 3 | <$5M | AI Deep Dive |
| Quali-Tee Screen Printing | Wholesale Trade | $21,663 | $21,743 | 3 | <$5M | AI Deep Dive |
| Winona Leasing Co. | Real Estate and Rental and Leasing | $21,516 | $21,657 | 2 | <$5M | AI Deep Dive |