| Sheridan Memorial Hospital Association | Health Care and Social Assistance | $1,343,800 | $1,348,798 | 111 | N/A |  Research |
| Diamond B Oilfield Trucking, Inc. | Transportation and Warehousing | $1,342,800 | $551,046 | 80 | $21.4M | Research |
| Diamond B Oilfield Trucking, Inc. | Transportation and Warehousing | $547,297 | $550,446 | 43 | $11.5M | Research |
| Black Diamond Well Services LLC | Mining, Quarrying, and Oil and Gas Extraction | $241,600 | $243,513 | 12 | <$5M | Research |
| Black Diamond Well Services LLC | Mining, Quarrying, and Oil and Gas Extraction | $241,600 | $242,878 | 14 | <$5M | Research |
| Ruebs Supervalu INC | Retail Trade | $238,400 | $239,713 | 41 | $10.2M | Research |
| Northern Oilfield Services | Mining, Quarrying, and Oil and Gas Extraction | $209,200 | $210,868 | 23 | <$5M | Research |
| Curtiss Farm & Auto | Retail Trade | $197,450 | $198,197 | 17 | <$5M | Research |
| Dennis Kanning | Construction | $144,573 | $145,274 | 1 | <$5M | Research |
| Farmers Union Oil Company of Plentywood Montana | Agriculture, Forestry, Fishing and Hunting | $128,093 | $117,473 | 9 | <$5M | Research |
| Plentywood Pharmacists PC | Retail Trade | $119,100 | $119,769 | 10 | <$5M | Research |
| Northern Oilfield Services Inc. | Mining, Quarrying, and Oil and Gas Extraction | $110,000 | $110,724 | 2 | <$5M | Research |
| Stevens Dental Group PC | Health Care and Social Assistance | $108,290 | $108,848 | 8 | <$5M | Research |
| Stevens Dental Group PC | Health Care and Social Assistance | $108,200 | $108,947 | 9 | <$5M | Research |
| Dennis Kanning DBA Kanning Concrete | Construction | $99,800 | $100,186 | 14 | <$5M | Research |
| Green River Lodging LLC | Accommodation and Food Services | $94,234 | $95,088 | 21 | $6.6M | Research |
| Michael Jensen | Accommodation and Food Services | $89,270 | $89,656 | 25 | <$5M | Research |
| Williston Parts Supply Co | Retail Trade | $83,700 | $84,266 | 13 | <$5M | Research |
| Glen-Wood INC | Health Care and Social Assistance | $80,600 | $81,141 | 25 | N/A | Research |
| Cousins Family Restaurant | Accommodation and Food Services | $75,100 | $75,643 | 26 | <$5M | Research |
| Quality Truck Repair, Inc. | Manufacturing | $72,000 | $72,440 | 7 | <$5M | Research |
| Quality Truck Repair, Inc. | Other Services (except Public Administration) | $71,982 | $72,406 | 7 | <$5M | Research |
| G.r. Nelson & Associates | Professional, Scientific, and Technical Services | $65,800 | $66,180 | 7 | <$5M | Research |
| Anderson Empire LLC | Accommodation and Food Services | $64,460 | $64,762 | 12 | <$5M | Research |
| Matildas Properties LLC | Accommodation and Food Services | $63,441 | $63,961 | 11 | <$5M | Research |