| James B Haggin Memorial Hospital Inc | Harrodsburg | E22Z Health Care | $37.8M | 22 |
| Crosswater Canyon Inc | Petersburg | A50 Arts, Culture & Humanities | $37.3M | 5 |
| EMHFL INC | Danville | E22 Health Care | $37M | 18 |
| Partners for Rural Impact Inc | Berea | B90 Education | $37M | 5 |
| UNITED STATES EQUESTRIAN FEDERATION INC | Lexington | N69 Recreation & Sports | $36.6M | 10 |
| DIG DEEPER FOUNDATION INC | Union | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $36.4M | 0 |
| NORTHERN KENTUCKY AREA DEVELOPMENT | Florence | S32 Community Improvement & Capacity Building | $36.2M | 1 |
| U OF L HEALTH - SHELBYVILLE INC | Louisville | E22 Health Care | $35.9M | 16 |
| HealthFirst Bluegrass Inc | Lexington | E32 Health Care | $34.9M | 8 |
| ASBURY THEOLOGICAL SEMINARY | Wilmore | B500 Education | $34.6M | 7 |
| KENTUCKY BLOOD CENTER INC | Lexington | E61Z Health Care | $34.5M | 8 |
| LICKING VALLEY RURAL ELECTRIC | West Liberty | — | $34.3M | 12 |
| KENTUCKY WESLEYAN COLLEGE | Owensboro | B420 Education | $33.7M | 9 |
| ISAIAH HOUSE INC | Willisburg | F22 Mental Health & Crisis Intervention | $33.4M | 10 |
| FOOTHILLS RURAL TELEPHONE COOPERATIVE | Staffordsville | — | $33.1M | 11 |
| UNITED STATES CATHOLIC CONFERENCE | Louisville | — | $32.8M | 7 |
| Christian Academy of Louisville Inc | Louisville | B20 Education | $32.7M | 6 |
| MOUNTAIN RURAL TELEPHONE | West Liberty | — | $32.5M | 12 |
| AMERICAN BOARD OF FAMILY MEDICINE INC | Lexington | — | $31.9M | 29 |
| BRECKINRIDGE HEALTH INC | Hardinsburg | E22Z Health Care | $31.7M | 7 |
| KENTON HOUSING INC | Latonia | L22Z Housing & Shelter | $31M | 7 |
| BAPTIST CONVALESCENT CENTER INC | Erlanger | P750 Human Services | $30.7M | 6 |
| CEDAR LAKE LODGE INC | Louisville | F33Z Mental Health & Crisis Intervention | $30.7M | 8 |
| DEACONESS UNION COUNTY HOSPITAL INC | Morganfield | E22 Health Care | $30.3M | 10 |
| TRIGG COUNTY HOSPITAL | Cadiz | E22Z Health Care | $30.2M | 10 |
| ALICE LLOYD COLLEGE | Pippa Passes | B420 Education | $30.1M | 3 |
| Healthpoint Family Care Inc | Newport | E30Z Health Care | $29M | 10 |
| KENTUCKY LABORERS DISTRICT COUNCIL | Lawrenceburg | — | $28.9M | 1 |
| MARSHALL COUNTY HOSPITAL DISTRICT | Benton | E220 Health Care | $28.8M | 7 |
| CALDWELL COUNTY HOSPITAL INC | Princeton | E22Z Health Care | $28.8M | 6 |
| BOYS & GIRLS CLUB WORKERS ASSOCIATION | Lexington | — | $28.6M | 0 |
| MEMBERS HERITAGE CREDIT UNION INC | Lexington | — | $27.8M | 6 |
| PARK DUVALLE COMMUNITY | Louisville | — | $27.8M | 13 |
| UNION COLLEGE | Barbourville | B430 Education | $27.6M | 7 |
| BIG SANDY RURAL ELECTRIC | Paintsville | — | $27.5M | 12 |
| SUNRISE CHILDREN'S SERVICES INC | Mt Washington | — | $27.2M | 2 |
| EAST CENTRAL ILLINOIS PIPETRADES | Lexington | — | $27.1M | 0 |
| BLUE GRASS COMMUNITY ACTION | Frankfort | P20Z Human Services | $27M | 1 |
| CCMH Corporation | Carrollton | E21 Health Care | $27M | 6 |
| CHRISTIAN CARE COMMUNITIES INC | Louisville | P750 Human Services | $26.9M | 9 |
| MEMBERS CHOICE CREDIT UNION | Ashland | — | $25.6M | 2 |
| KCEOC COMMUNITY ACTION PARTNERSHIP INC | Barbourville | B22Z Education | $25.6M | 4 |
| CONSTRUCTION INDUSTRY HEALTH AND | Lexington | — | $25.5M | 0 |
| WENDELL FOSTER'S CAMPUS FOR | Owensboro | G23 Diseases, Disorders & Medical Disciplines | $25.5M | 3 |
| FEEDING AMERICA KENTUCKY'S HEARTLAND | Elizabethtown | K31Z Food, Agriculture & Nutrition | $25.4M | 0 |
| Association Healthcare Consortium Inc | Louisville | Y43 Mutual & Membership Benefit | $25.1M | 0 |
| WAYNE COUNTY HOSPITAL INC | Monticello | E220 Health Care | $25M | 13 |
| ABFM FOUNDATION INC | Lexington | P80 Human Services | $25M | 9 |
| Transcend Credit Union | Louisville | — | $24.5M | 9 |
| EASTERN KENTUCKY CONCENTRATED EMPLOYMENT PROGRAM INC | Hazard | J22Z Employment | $23.8M | 3 |
