| Cimarron Casino Enterprise | Accommodation and Food Services | $1,878,100 | $1,895,107 | 250 | N/A |  Research |
| Cimarron Casino Enterprise-A Component Unit of the Iowa Trib | Arts, Entertainment, and Recreation | $1,872,852 | $1,885,129 | 187 | N/A | Research |
| Ioway Maintenance Inc. | Administrative and Support and Waste Management | $238,098 | $239,507 | 46 | $10.0M | Research |
| Ralph's Packing Company, Inc. | Retail Trade | $218,977 | $220,321 | 39 | <$5M | Research |
| Sugar and Spice LLC | Accommodation and Food Services | $198,873 | $200,221 | 35 | $6.2M | Research |
| Sugar and Spice, LLC | Accommodation and Food Services | $144,711 | $146,455 | 52 | $9.2M | Research |
| Cimarron Valley Coop, Inc. | Public Administration | $143,222 | $144,093 | 19 | N/A | Research |
| Perkins Veterinary Clinic LLC | Professional, Scientific, and Technical Services | $139,179 | $140,038 | 18 | <$5M | Research |
| Blackjack Construction LLC | Construction | $137,693 | $138,734 | 12 | <$5M | Research |
| C & R Manufacturing & Supply, | Retail Trade | $117,500 | $118,721 | 13 | <$5M | Research |
| High Country Contractors INC | Construction | $104,611 | $105,009 | 11 | $12.5M | Research |
| High Country Contractors INC | Construction | $99,873 | $100,530 | 10 | <$5M | Research |
| Red Bud Assisted Living, LLC | Health Care and Social Assistance | $98,600 | $99,096 | 16 | <$5M | Research |
| Country Comfort Heating & Air Conditioning, Inc. | Construction | $88,500 | $89,327 | 10 | <$5M | Research |
| Ioway Accounting Services, Inc. | Professional, Scientific, and Technical Services | $86,824 | $87,410 | 13 | <$5M | Research |
| Frank's Diesel Service, Inc. | Other Services (except Public Administration) | $86,783 | $87,310 | 8 | <$5M | Research |
| Frank's Diesel Service Inc. | Other Services (except Public Administration) | $86,269 | $86,834 | 7 | <$5M | Research |
| Double L Welding & Construction | Manufacturing | $81,200 | $81,914 | 7 | <$5M | Research |
| Tech Inc. | Manufacturing | $80,634 | $81,172 | 6 | $6.0M | Research |
| Resolutions Counseling Group | Health Care and Social Assistance | $78,164 | $78,802 | 6 | <$5M | Research |
| Resolutions Counseling Group | Health Care and Social Assistance | $73,383 | $74,206 | 4 | <$5M | Research |
| Rains Diesel Repair LLC | Other Services (except Public Administration) | $68,355 | $68,703 | 6 | <$5M | Research |
| Cimarron Mechanical INC | Construction | $67,111 | $88,998 | 8 | <$5M | Research |
| Tech II LLC | Professional, Scientific, and Technical Services | $66,292 | $66,773 | 9 | <$5M | Research |
| Benchmark Animal Hospital and Equine Podiatry Center, LLC | Professional, Scientific, and Technical Services | $65,300 | $65,668 | 7 | <$5M | Research |