| New Horizons Woodworks INC | Manufacturing | $274,800 | $277,014 | 28 | $7.3M |  Research |
| Siskiyou Initiative | Educational Services | $271,673 | $273,511 | 27 | <$5M | Research |
| Siskiyou Eye Center Medical Group PC | Health Care and Social Assistance | $270,982 | $274,618 | 23 | $7.2M | Research |
| Hammond Family Corporation of Ashland | Retail Trade | $267,435 | $269,076 | 30 | $6.5M | Research |
| Hammond Family Corporation of Ashland | Retail Trade | $267,400 | $270,968 | 35 | $7.6M | Research |
| Siskiyou School | Educational Services | $264,337 | $267,357 | 30 | <$5M | Research |
| Phytonyx | Agriculture, Forestry, Fishing and Hunting | $259,995 | $263,534 | 24 | <$5M | Research |
| Valley View Auto Repair | Other Services (except Public Administration) | $258,400 | $259,795 | 24 | <$5M | Research |
| Brickroom, LLC | Accommodation and Food Services | $253,382 | $255,124 | 55 | $17.2M | Research |
| Warren Resort Hotels of Oregon Inc. | Accommodation and Food Services | $246,883 | $248,675 | 16 | $5.0M | Research |
| Ashland Supportive Housing Comm Outreach | Health Care and Social Assistance | $241,715 | $244,166 | 31 | N/A | Research |
| Caldera Catering & Events LLC | Accommodation and Food Services | $236,470 | $239,553 | 45 | $8.4M | Research |
| Solid Ground Landscape Inc. | Professional, Scientific, and Technical Services | $235,802 | $237,625 | 22 | <$5M | Research |
| Warren Resort Hotels of Ashlandinc. | Accommodation and Food Services | $235,525 | $237,190 | 24 | $7.5M | Research |
| Jolly Dog Tag INC | Accommodation and Food Services | $232,530 | $234,358 | 32 | $5.7M | Research |
| True South Solar INC | Construction | $229,450 | $230,937 | 16 | $5.3M | Research |
| Winchester Inn, LLC | Accommodation and Food Services | $227,900 | $230,610 | 25 | $7.8M | Research |
| Ashco INC | Accommodation and Food Services | $226,052 | $228,313 | 30 | $5.3M | Research |
| Oregon Cabaret Theatre INC | Arts, Entertainment, and Recreation | $224,500 | $227,003 | 50 | $8.2M | Research |
| Oregon Cabaret Theatre, Inc. | Arts, Entertainment, and Recreation | $224,500 | $226,271 | 51 | $8.4M | Research |
| Tl Forest Products INC | Agriculture, Forestry, Fishing and Hunting | $222,000 | $223,622 | 23 | <$5M | Research |
| Louie's Bar & Grill, LLC | Accommodation and Food Services | $218,700 | $220,318 | 35 | $6.2M | Research |
| Roberts Irvine Vineyards LLC | Accommodation and Food Services | $217,777 | $218,981 | 300 | $36.8M | Research |
| T L Forest Products Inc. | Agriculture, Forestry, Fishing and Hunting | $216,789 | $217,882 | 22 | <$5M | Research |
| Ashland General Hardware Inc. | Retail Trade | $215,000 | $216,451 | 33 | $6.8M | Research |