| KVC BEHAVIORAL HEALTHCARE KENTUCKY INC | Lexington | F30 Mental Health & Crisis Intervention | $26.5M | 8 |
| EASTERN KENTUCKY CONCENTRATED EMPLOYMENT PROGRAM INC | Hazard | J22Z Employment | $26.3M | 2 |
| EMPLOYMENT SOLUTIONS INC | Lexington | J30Z Employment | $26M | 3 |
| SUNRISE CHILDREN'S SERVICES INC | Mt Washington | — | $25.9M | 3 |
| KENTUCKY RIVER AREA DEVELOPMENT DISTRICT | Hazard | — | $25.7M | 1 |
| MEMBERS CHOICE CREDIT UNION | Ashland | — | $25.6M | 2 |
| KCEOC COMMUNITY ACTION PARTNERSHIP INC | Barbourville | B22Z Education | $25.6M | 4 |
| CONSTRUCTION INDUSTRY HEALTH AND WELFARE TRUST | Lexington | — | $25.5M | 0 |
| WENDELL FOSTER'S CAMPUS FOR DEVELOPMENTAL DISABILITIES INC | Owensboro | G23 Diseases, Disorders & Medical Disciplines | $25.5M | 3 |
| FEEDING AMERICA KENTUCKY'S HEARTLAND INC | Elizabethtown | K31Z Food, Agriculture & Nutrition | $25.4M | 0 |
| LEXINGTON SCHOOL INC | Lexington | B25Z Education | $25.4M | 5 |
| CENTRAL KENTUCKY COMMUNITY ACTION COUNCIL INC | Lebanon | P20Z Human Services | $25.2M | 3 |
| WAYNE COUNTY HOSPITAL INC | Monticello | E220 Health Care | $25M | 13 |
| ABFM FOUNDATION INC | Lexington | P80 Human Services | $25M | 9 |
| LEXINGTON PUBLIC LIBRARY | Lexington | B71Z Education | $24.7M | 4 |
| LIMESTONE FAMILY FOUNDATION INC C/O GLENVIEW TRUST COMPANY | Louisville | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $24.4M | 0 |
| RURAL TRANSIT ENTERPRISES COORDINATED INC | Mount Vernon | P52Z Human Services | $24M | 2 |
| REGIONAL HEALTH CARE AFFILIATES INC | Providence | E32 Health Care | $23.5M | 10 |
| LAUREL HOUSING INC DBA LAUREL HEIGHTS HOME FOR THE ELDERLY | London | P75 Human Services | $23.4M | 6 |
| MIRAMAR CHARITABLE FOUNDATION | Ft Mitchell | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $23.1M | 1 |
| PEOPLES RURAL TELEPHONE COOPERATIVE CORPORATION | McKee | — | $22.9M | 13 |
| CUMBERLAND COUNTY HOSPITAL ASSOCIATION INC | Burkesville | E22I Health Care | $22.8M | 13 |
| ZEROV INC | Frankfort | I710 Crime & Legal-Related | $22.7M | 0 |
| IBEW LOCAL NO 150 WELFARE FUND | Lexington | — | $22.7M | 1 |
| FEDERATION OF APPALACHIAN HOUSING ENTERPRISES INC | Berea | L020 Housing & Shelter | $22.4M | 8 |
| COMMUNITY VENTURES CORPORATION | Lexington | S99Z Community Improvement & Capacity Building | $22.2M | 16 |
| JEANNE D'ARC RESIDENCE | Melbourne | P70Z Human Services | $22.1M | 0 |
| TJ HEALTH COLUMBIA INC | Glasgow | E22 Health Care | $22M | 10 |
| CONSTRUCTION INDUSTRY OF KANSAS HEALTH & WELFARE FUND | Lexington | — | $21.9M | 0 |
| ASHLAND CREDIT UNION | Ashland | — | $21.9M | 1 |
| KENTUCKY COUNTRY DAY SCHOOL INC | Louisville | B200 Education | $21.7M | 8 |
| KENTUCKY RIVER FOOTHILLS DEVELOPMENT COUNCIL INC | Richmond | S200 Community Improvement & Capacity Building | $21.6M | 4 |
| SAYRE CHRISTIAN VILLAGE NURSING HOME INC | Lexington | E91Z Health Care | $21.5M | 7 |
| KOSAIR CHARITIES COMMITTEE INC | Louisville | E120 Health Care | $21.5M | 7 |
| THE WHAS CRUSADE FOR CHILDREN INC | Louisville | — | $21.1M | 2 |
| JEWISH HERITAGE FUND FOR EXCELLENCE INC | Louisville | E19 Health Care | $20.9M | 2 |
| PENNYRILE ALLIED COMMUNITY SERVICES INC | Hopkinsville | S200 Community Improvement & Capacity Building | $20.9M | 2 |
| MONROE MEDICAL FOUNDATION INC | Tompkinsville | E22Z Health Care | $20.9M | 9 |
| RAMEY-ESTEP HOMES INC | Rush | P730 Human Services | $20.8M | 5 |
| THE MEDICAL CENTER AT CLINTON COUNTY INC | Bowling Green | E22 Health Care | $20.8M | 11 |
| BRESCIA UNIVERSITY INC | Owensboro | B42Z Education | $20.8M | 10 |
| Disabled American Veterans (DAV) Charitable Service Trust | Erlanger | W110 Public & Societal Benefit | $20.8M | 0 |
| HACET FOUNDATION INC | Prospect | T99 Philanthropy, Voluntarism & Grantmaking Foundations | $20.8M | 0 |
| KENTUCKY EDUCATIONAL DEVELOPME CORPORATION | Ashland | — | $20.7M | 1 |
| YOUNG MEN'S CHRISTIAN ASSOCIATION OF GREATER LEXINGTON KENTUCKY | Lexington | — | $20.6M | 6 |
| MARYHURST INC | Louisville | O99 Youth Development | $20.5M | 3 |
| KENTUCKY HIGHLANDS INVESTMENT CORP | London | — | $20.3M | 17 |
| JUNIPER HEALTH INC | Beattyville | E21 Health Care | $20.1M | 5 |
| BIG SANDY AREA COMMUNITY ACTION PROGRAM INC | Paintsville | — | $20.1M | 1 |
| LEXINGTON CHRISTIAN ACADEMY | Lexington | B200 Education | $19.8M | 3 |
