| GATEWAY COMMUNITY SERVICES ORGANIZATION | West Liberty | S80Z Community Improvement & Capacity Building | $17.9M | 1 |
| LEARNING GROVE INC | Covington | — | $17.8M | 4 |
| THE COMMUNITY FOUNDATION OF LOUISVILLE | Louisville | T31Z Philanthropy, Voluntarism & Grantmaking Foundations | $17.7M | 7 |
| SAYRE SCHOOL | Lexington | B200 Education | $17.4M | 4 |
| KENTUCKY EDUCATIONAL TELEVISION | Lexington | A320 Arts, Culture & Humanities | $17.1M | 14 |
| SPEED ART MUSEUM | Louisville | A510 Arts, Culture & Humanities | $17.1M | 5 |
| LOUISVILLE THEATRICAL ASSOCIATION INC | Louisville | A610 Arts, Culture & Humanities | $16.9M | 0 |
| NORTHEAST KY COMMUNITY ACTION AGENCY | Olive Hill | P200 Human Services | $16.9M | 1 |
| WILLIAM LAWRENCE AND BLANCHE HUGHES | Lexington | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $16.6M | 0 |
| COMMUNITY ACTION OF SOUTHERN KENTUCKY | Bowling Green | — | $16.3M | 0 |
| SERVICE ONE CREDIT UNION INC | Bowling Green | — | $16.3M | 6 |
| ELECTRICAL WORKERS LOCAL #369 IBEW | Louisville | — | $16.3M | 5 |
| Humana Foundation Inc | Louisville | — | $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 |
| KENTUCKY ASSN OF SEXUAL ASSAULT | Frankfort | — | $15.8M | 2 |
| MURRAY STATE UNIVERSITY FOUNDATION INC | Murray | B110 Education | $15.7M | 4 |
| METRO UNITED WAY INC | Louisville | T700 Philanthropy, Voluntarism & Grantmaking Foundations | $15.7M | 7 |
| Brighton Center Inc | Newport | — | $15.7M | 2 |
| KENTUCKY MOUNTAIN HEALTH ALLIANCE I | Hazard | E32 Health Care | $15.6M | 4 |
| KENTUCKY PRIMARY CARE ASSOCIATION INC | Frankfort | E20C Health Care | $15.6M | 0 |
| INTERNATIONAL COACHING FEDERATION | Lexington | S41 Community Improvement & Capacity Building | $15.5M | 0 |
| PHP INC | Hopkinsville | — | $15.5M | 0 |
| Independent Pilots Association | Louisville | — | $15.2M | 13 |
| CAVE HILL INVESTMENT CO | Louisville | — | $15.2M | 2 |
| MICHAEL AND CHANDRA RUDD FOUNDATION INC | Louisville | T20Z Philanthropy, Voluntarism & Grantmaking Foundations | $15.2M | 0 |
| RAMEY-ESTEP HOMES INC | Rush | P730 Human Services | $15M | 4 |
| THE THIRD AND OAK CORPORATION DBA | Louisville | P750 Human Services | $15M | 7 |
| COMMUNITY HOSPICE INC | Ashland | — | $14.9M | 5 |
| THE GHEENS FOUNDATION INC | Louisville | — | $14.9M | 7 |
| NORTON HEALTHCARE FOUNDATION INC | Louisville | E122 Health Care | $14.8M | 13 |
| RAY & KAY ECKSTEIN CHARITABLE TRUST | Paducah | B82 Education | $14.7M | 0 |
| BLESSINGS IN A BACKPACK INC | Louisville | P60 Human Services | $14.4M | 7 |
| International Union UAW Local 862 | Louisville | — | $14.4M | 21 |
| GREEN RIVER REGIONAL | Bowling Green | B80 Education | $14.3M | 1 |
| PLUMBERS AND PIPEFITTERS LOCAL 502 | Louisville | — | $14.2M | 4 |
| COVINGTON LIFE SCIENCES PARTNERS INC | Covington | — | $14.1M | 0 |
| LIVWELL COMMUNITY HEALTH SERVICES INC | Paducah | G81 Diseases, Disorders & Medical Disciplines | $14.1M | 1 |
| FAMILY & CHILDREN'S PLACE INC | Louisville | P460 Human Services | $13.8M | 3 |
| HABITAT FOR HUMANITY OF METRO LOUISVILLE | Louisville | L20Z Housing & Shelter | $13.8M | 1 |
| JEWISH COMMUNITY OF LOUISVILLE INC | Louisville | T70 Philanthropy, Voluntarism & Grantmaking Foundations | $13.7M | 4 |
| BIG SPRING COUNTRY CLUB INC | Louisville | — | $13.7M | 6 |
| METHODIST HOME OF KENTUCKY INC | Nicholasville | P20 Human Services | $13.7M | 1 |
| Horizon Community Funds of Northern | Covington | T31 Philanthropy, Voluntarism & Grantmaking Foundations | $13.7M | 3 |
| ODYSSEY INC | Louisa | F212 Mental Health & Crisis Intervention | $13.7M | 0 |
| USPIRITUS INC (BELLEWOOD & BROOKLAWN) | Louisville | F01 Mental Health & Crisis Intervention | $13.6M | 1 |
| Community Health Centers of Western Kentucky Inc | Greenville | E20 Health Care | $13.5M | 8 |
| HOSPICE OF HOPE INC | Maysville | P740 Human Services | $13.5M | 6 |
| BLUEGRASS PRIMARY HEALTH CARE CENTER | Lexington | E32 Health Care | $13.4M | 11 |
