| REGIONAL HEALTH CARE AFFILIATES INC | Providence | E32 Health Care | $23.5M | 10 |
| THE LOUISVILLE URBAN LEAGUE INC | Louisville | P22Z Human Services | $23.4M | 6 |
| EMPLOYMENT SOLUTIONS INC | Lexington | J30Z Employment | $23.4M | 2 |
| LEXINGTON PUBLIC LIBRARY | Lexington | B71Z Education | $23.2M | 2 |
| Northern Kentucky Community Action | Covington | — | $23M | 2 |
| CUMBERLAND COUNTY HOSPITAL ASSOCIATION | Burkesville | E22I Health Care | $22.8M | 13 |
| RURAL TRANSIT ENTERPRISES COORDINATED INC | Mount Vernon | P52Z Human Services | $22.7M | 2 |
| CENTRAL KENTUCKY COMMUNITY ACTION | Lebanon | P20Z Human Services | $22.5M | 2 |
| FEDERATION OF APPALACHIAN HOUSING | Berea | L020 Housing & Shelter | $22.4M | 8 |
| LIVINGSTON HOSPITAL & HEALTHCARE | Salem | E220 Health Care | $22.3M | 6 |
| 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 |
| KVC BEHAVIORAL HEALTHCARE KENTUCKY INC | Lexington | F30 Mental Health & Crisis Intervention | $22M | 9 |
| ASHLAND CREDIT UNION | Ashland | — | $21.9M | 1 |
| KENTUCKY HOSPITAL ASSOCIATION | Louisville | — | $21.9M | 33 |
| LOUISVILLE COLLEGIATE SCHOOL | Louisville | B200 Education | $21.8M | 6 |
| KENTUCKY COUNTRY DAY SCHOOL INC | Louisville | B200 Education | $21.7M | 8 |
| PEOPLES RURAL TELEPHONE | McKee | — | $21.6M | 12 |
| KENTUCKY RIVER FOOTHILLS | Richmond | S200 Community Improvement & Capacity Building | $21.6M | 4 |
| SAYRE CHRISTIAN VILLAGE NURSING HOME | Lexington | E91Z Health Care | $21.5M | 7 |
| KOSAIR CHARITIES COMMITTEE INC | Louisville | E120 Health Care | $21.5M | 7 |
| MATTHEW 25 AIDS SERVICES INC | Henderson | E600 Health Care | $21.4M | 1 |
| LOUISVILLE MEDICAL CENTER DEVELOPMENT | Louisville | — | $21.4M | 0 |
| THE WHAS CRUSADE FOR CHILDREN INC | Louisville | — | $21.1M | 2 |
| NEW DIRECTIONS HOUSING CORPORATION | Louisville | — | $21M | 7 |
| 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 |
| 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 |
| ZEROV INC | Frankfort | I710 Crime & Legal-Related | $20.8M | 0 |
| KENTUCKY EDUCATIONAL DEVELOPME | Ashland | — | $20.7M | 1 |
| CONSTRUCTION INDUSTRY OF KANSAS | Lexington | — | $20.7M | 0 |
| LAUREL HOUSING INC DBA | London | P75 Human Services | $20.5M | 6 |
| YOUNG MEN'S CHRISTIAN ASSOCIATION | Lexington | — | $20.5M | 7 |
| 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 | Paintsville | — | $20.1M | 1 |
| LEXINGTON SCHOOL INC | Lexington | B25Z Education | $19.9M | 5 |
| LEXINGTON CHRISTIAN ACADEMY | Lexington | B200 Education | $19.8M | 3 |
| THE CHILDREN'S HOSPITAL FOUNDATION INC | Louisville | E110 Health Care | $19.8M | 12 |
| KENTUCKY CHRISTIAN UNIVERSITY | Grayson | B58Z Education | $19.5M | 1 |
| KENTUCKY REFUGEE MINISTRIES INC | Louisville | X99 Religion-Related | $19.1M | 4 |
| MASONIC HOME INDEPENDENT LIVING II LLC | Masonic Home | L22 Housing & Shelter | $18.7M | 5 |
| LAKE CUMBERLAND COMMUNITY ACTION | Jamestown | P200 Human Services | $18.7M | 0 |
| Northern Kentucky Cooperative for | Cold Spring | B99 Education | $18.6M | 7 |
| HENDERSON COUNTY HEALTH CARE CORPORATION | Henderson | E21Z Health Care | $18.5M | 8 |
| NATIONAL CORVETTE MUSEUM FOUNDATION INC | Bowling Green | A500 Arts, Culture & Humanities | $18.2M | 6 |
