| KENTUCKY CHRISTIAN UNIVERSITY | Grayson | B58Z Education | $19.5M | 1 |
| NATIONAL CORVETTE MUSEUM FOUNDATION INC | Bowling Green | A500 Arts, Culture & Humanities | $19.5M | 10 |
| Northern Kentucky Community Action Commission Inc | Covington | — | $19.2M | 2 |
| 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 |
| Northern Kentucky Cooperative for Educational Services Inc | Cold Spring | B99 Education | $18.6M | 7 |
| LAKE CUMBERLAND COMMUNITY ACTION AGENCY INC | Jamestown | P200 Human Services | $18M | 0 |
| HENDERSON COUNTY HEALTH CARE CORPORATION | Henderson | E21Z Health Care | $18M | 7 |
| METHODIST HOME OF KENTUCKY INC | Nicholasville | P20 Human Services | $18M | 1 |
| THE COMMUNITY FOUNDATION OF LOUISVILLE DEPOSITORY INC | Louisville | T31Z Philanthropy, Voluntarism & Grantmaking Foundations | $17.9M | 7 |
| GATEWAY COMMUNITY SERVICES ORGANIZATION INC | West Liberty | S80Z Community Improvement & Capacity Building | $17.9M | 1 |
| LEARNING GROVE INC | Covington | — | $17.8M | 4 |
| SERVICE ONE CREDIT UNION INC | Bowling Green | — | $17.6M | 9 |
| SAYRE SCHOOL | Lexington | B200 Education | $17.4M | 4 |
| Simmons College of Kentucky Inc | Louisville | B43 Education | $17.3M | 4 |
| COMMUNITY HOSPICE INC | Ashland | — | $17.2M | 5 |
| KENTUCKY EDUCATIONAL TELEVISION FOUNDATION | Lexington | A320 Arts, Culture & Humanities | $17.1M | 14 |
| NEW DIRECTIONS HOUSING CORPORATION | Louisville | — | $17.1M | 7 |
| SPEED ART MUSEUM | Louisville | A510 Arts, Culture & Humanities | $17.1M | 5 |
| NORTHEAST KY COMMUNITY ACTION AGENCY INC | Olive Hill | P200 Human Services | $17.1M | 1 |
| METRO UNITED WAY INC | Louisville | T700 Philanthropy, Voluntarism & Grantmaking Foundations | $16.9M | 7 |
| THE THIRD AND OAK CORPORATION DBA TREYTON OAK TOWERS | Louisville | P750 Human Services | $16.7M | 8 |
| WILLIAM LAWRENCE AND BLANCHE HUGHES FOUNDATION INC | Lexington | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $16.6M | 0 |
| COMMUNITY ACTION OF SOUTHERN KENTUCKY INC | Bowling Green | — | $16.3M | 0 |
| THE GREATER LOUISVILLE WORKFORCE DEVELOPMENT BOARD INC | Louisville | S31 Community Improvement & Capacity Building | $16.3M | 3 |
| ELECTRICAL WORKERS LOCAL #369 IBEW | Louisville | — | $16.3M | 5 |
| Independent Pilots Association | Louisville | — | $16.2M | 12 |
| KENTUCKY PRIMARY CARE ASSOCIATION INC | Frankfort | E20C Health Care | $16.2M | 0 |
| Humana Foundation Inc | Louisville | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $16.2M | 0 |
| DANIEL BOONE COMMUNITY ACTION AGENCY | Manchester | P200 Human Services | $16.1M | 3 |
| LIFESKILLS HEALTH SERVICES INC | Bowling Green | E60 Health Care | $15.9M | 0 |
| KENTUCKY FARM BUREAU FEDERATION | Louisville | — | $15.9M | 15 |
| THE SCRIPPS FAMILY FUND FOR EDUCATION AND THE ARTS | Ft Mitchell | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $15.9M | 0 |
| KENTUCKY ASSN OF SEXUAL ASSAULT PROGRAMS INC | Frankfort | — | $15.8M | 2 |
| MURRAY STATE UNIVERSITY FOUNDATION INC | Murray | B110 Education | $15.7M | 4 |
| CONTINUING CARE HOSPITAL INC | Lexington | — | $15.7M | 12 |
| JEWISH COMMUNITY OF LOUISVILLE INC | Louisville | T70 Philanthropy, Voluntarism & Grantmaking Foundations | $15.5M | 3 |
| INTERNATIONAL COACHING FEDERATION GLOBAL ENTERPRISE INC | Lexington | S41 Community Improvement & Capacity Building | $15.5M | 0 |
| PHP INC | Hopkinsville | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $15.5M | 0 |
| ASHLAND NURSING HOME CORP | Ashland | E91 Health Care | $15.4M | 8 |
| CAVE HILL INVESTMENT CO | Louisville | — | $15.2M | 2 |
| MICHAEL AND CHANDRA RUDD FOUNDATION INC | Louisville | T20Z Philanthropy, Voluntarism & Grantmaking Foundations | $15.2M | 0 |
| THE GHEENS FOUNDATION INC | Louisville | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $14.9M | 7 |
| HOSPICE OF HOPE INC | Maysville | P740 Human Services | $14.8M | 7 |
| NORTON HEALTHCARE FOUNDATION INC | Louisville | E122 Health Care | $14.8M | 13 |
| COMMONWEALTH CREDIT UNION | Frankfort | — | $14.7M | 8 |
| BLESSINGS IN A BACKPACK INC | Louisville | P60 Human Services | $14.4M | 7 |
| International Union UAW Local 862 | Louisville | — | $14.4M | 21 |
| JAMES GRAHAM BROWN FOUNDATION INC | Louisville | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $14.3M | 16 |
| GREEN RIVER REGIONAL EDUCATIONAL COOPERATIVE | Bowling Green | B80 Education | $14.3M | 1 |
