| 1 | saint mary's university of minnesota center for business analytics | $211.5M | 3,000 | 70 | B |
| 2 | Merchants Bank NA | $73.6M | 350 | 60 | C+ |
| 3 | Merchants Bank, National Association (Winona, MN) | $73.6M | 350 | 60 | C+ |
| 4 | WINONA AGENCY, INC | $45.9M | 125 | 60 | C+ |
| 5 | ODIN Casting | $33.3M | 125 | 60 | C+ |
| 6 | Winona Heating & Ventilating, Inc. | $25.0M | 125 | 60 | C+ |
| 7 | WELCH EXCAVATION AND UTILITY COMPANY INCORPORATED | $18.9M | 125 | 60 | C+ |
| 8 | Hiawatha Broadband Communications, Inc | $14.6M | 125 | 60 | C+ |
| 9 | Phi Theta Chi | $14.3M | 125 | 60 | C+ |
| 10 | winona r-iii school district | $14.3M | 125 | 60 | C+ |
| 11 | ANOVA | $12.2M | 30 | 60 | C+ |
| 12 | Teakworks4u, LLC | $12.2M | 30 | 60 | C+ |
| 13 | Croix Retail | $12.2M | 30 | 60 | C+ |
| 14 | Dahl Chevrolet-Buick-GMC, Inc. | $12.2M | 30 | 60 | C+ |
| 15 | mon petit cupcake | $12.2M | 30 | 60 | C+ |
| 16 | Alliant Castings, Inc. | $8.0M | 30 | 50 | C |
| 17 | Midwest Metal Products, Inc (MMP) | $8.0M | 30 | 50 | C |
| 18 | JR WATKINS INC | $7.4M | 30 | 50 | C |
| 19 | Badger Equipment Co | $7.0M | 30 | 50 | C |
| 20 | Mach-B Grinding Wheel Shaping & Resizing, a division of Goodson Shop Supplies | $7.0M | 30 | 50 | C |
| 21 | Douglas Machining Services, LLC | $6.6M | 30 | 50 | C |
| 22 | Hiatt Metal Forming, LLC | $6.6M | 30 | 50 | C |
| 23 | Hh Services | $6.3M | 30 | 50 | C |
| 24 | The Merchants Trust | $6.3M | 30 | 50 | C |
| 25 | mugby junction | $6.0M | 30 | 50 | C |
| 26 | east texas wildflower honey farm | $6.0M | 30 | 50 | C |
| 27 | Sugar Loaf Ford Lincoln | $5.9M | 30 | 50 | C |
| 28 | Hiatt Manufacturing Inc | $5.7M | 30 | 50 | C |
| 29 | Kennedy Business Systems Inc | $5.1M | 30 | 50 | C |
| 30 | ericksen hearing services, llc | $5.0M | 30 | 50 | C |
| 31 | Days Inn Winona | $4.9M | 30 | 50 | C |
| 32 | westfield golf club inc | $4.9M | 30 | 50 | C |
| 33 | Hawkins Ash CPAs - Winona | $4.6M | 125 | 50 | C |
| 34 | WAPASHA CONSTRUCTION CO. | $4.5M | 30 | 50 | C |
| 35 | Southern Shade Tree Co | $4.5M | 30 | 50 | C |
| 36 | potter construction, llc - georgia/south carolina | $4.5M | 30 | 50 | C |
| 37 | Scharmer & Sons | $4.5M | 30 | 50 | C |
| 38 | busby’s roofing | $4.5M | 30 | 50 | C |
| 39 | Associated Crafts & Willet Hauser Architectural Glass | $4.5M | 125 | 50 | C |
| 40 | Koehler Construction | $3.8M | 30 | 50 | C |
| 41 | Felix Farm | $3.8M | 5 | 50 | C |
| 42 | WINONA CHRISTIAN SCHOOL | $3.4M | 30 | 50 | C |
| 43 | BLUFFVIEW MONTESSORI SCHOOL | $3.4M | 30 | 50 | C |
| 44 | FUGITIVE INVESTIGATIONS | $3.0M | 30 | 50 | C |
| 45 | Winona Fire Dept | $3.0M | 30 | 50 | C |
| 46 | Winona Workforce Center | $3.0M | 30 | 50 | C |
| 47 | economy specialty services, llc | $2.9M | 30 | 50 | C |
| 48 | VCS Technologies | $2.8M | 30 | 50 | C |
| 49 | kate + bella | $2.8M | 30 | 50 | C |
| 50 | sugar loaf antiques & crafts | $2.8M | 30 | 50 | C |
| 51 | winona feed seed & more | $2.8M | 30 | 50 | C |
| 52 | LarLu | $2.7M | 125 | 50 | C |
| 53 | saint croix | $2.6M | 125 | 50 | C |
| 54 | Steak Shop Catering Service | $2.5M | 5 | 50 | C |
| 55 | Schott Distributing Co | $2.1M | 5 | 50 | C |
| 56 | Daniels Ace Hardware Yamaha | $2.0M | 5 | 50 | C |
| 57 | P3 Plastics | $2.0M | 5 | 50 | C |
| 58 | Severson Transport Inc | $2.0M | 5 | 50 | C |
| 59 | Jell Industrial Services Inc | $1.8M | 5 | 50 | C |
| 60 | merchants trust company | $1.8M | 30 | 50 | C |
| 61 | Winona Manor | $1.6M | 30 | 50 | C |
| 62 | Brosnahan Law Firm | $1.5M | 30 | 50 | C |
| 63 | Kuehner Law Office | $1.5M | 30 | 50 | C |
| 64 | Hiawatha Valley Education Dist | $1.5M | 125 | 50 | C |
| 65 | CDL Helpers | $1.4M | 5 | 50 | C |
| 66 | Philipps Bus Service Inc | $1.4M | 5 | 50 | C |
| 67 | tlougan rusco | $1.3M | 5 | 50 | C |
| 68 | West Import | $1.3M | 5 | 50 | C |
| 69 | Rogers Meats | $1.2M | 5 | 50 | C |
| 70 | wellington’s pub & grill | $1.2M | 30 | 50 | C |
| 71 | suds stor & more | $1.2M | 30 | 50 | C |
| 72 | meier plumbing & heating | $1.2M | 30 | 50 | C |
| 73 | dee’s auto care specialists | $1.2M | 30 | 50 | C |
| 74 | Engineered Sheet Products | $1.1M | 5 | 50 | C |
| 75 | Woodshed Technologies Inc | $1.1M | 5 | 50 | C |
| 76 | Conrad Solutions | $1.1M | 5 | 50 | C |
| 77 | Weldfabulous (Online Welding Supplies | Welding Supplies | PPE ) | $1.1M | 5 | 50 | C |
| 78 | Bloedow Bakery Shop | $1.1M | 5 | 50 | C |
| 79 | Mcnally Realty Llp | $1.1M | 5 | 50 | C |
| 80 | College Bound, Inc. | $1.1M | 5 | 50 | C |
| 81 | Asphalt Armor Sealcoating | $1.0M | 5 | 40 | D |
| 82 | Lattman Cycle Design Machining | $992K | 5 | 40 | D |
| 83 | Gilmore Avenue Car Wash & Lube | $992K | 5 | 40 | D |
| 84 | Delta Sigma Pi - Kappa Upsilon | $988K | 30 | 40 | D |
| 85 | Gundersen National Child Protection Training Center | $988K | 30 | 40 | D |
| 86 | car jack auto | $951K | 5 | 40 | D |
| 87 | brians cars | $951K | 5 | 40 | D |
| 88 | underdahl toyota of winona | $951K | 5 | 40 | D |
| 89 | papenfuss salvage | $951K | 5 | 40 | D |
| 90 | Motorsports Training | $951K | 5 | 40 | D |
| 91 | Northland Automation | $950K | 5 | 40 | D |
| 92 | Winona State Hackathon | $851K | 5 | 40 | D |
| 93 | Renowne, LLC | $851K | 5 | 40 | D |
| 94 | Brewer Investments | $851K | 5 | 40 | D |
| 95 | Probuild North Llc | $851K | 5 | 40 | D |
| 96 | White Owl Enterprises | $851K | 5 | 40 | D |
| 97 | thompson realty & appraisal | $845K | 30 | 40 | D |
| 98 | triplains usd 275 | $834K | 5 | 40 | D |
| 99 | Infinity Chiropractic Wellness | $834K | 5 | 40 | D |
| 100 | the connection a chiropractic place | $834K | 5 | 40 | D |