| Central Kentucky Management Services Inc | Lexington | E8XZ Health Care | $39.6M | 10 |
| AMERICAN PRINTING HOUSE FOR THE BLIND INC | Louisville | A330 Arts, Culture & Humanities | $39.4M | 13 |
| ISAIAH HOUSE INC | Willisburg | F22 Mental Health & Crisis Intervention | $39.1M | 9 |
| THE MEDICAL CENTER AT FRANKLIN INC | Bowling Green | E220 Health Care | $38.9M | 12 |
| LICKING VALLEY RURAL ELECTRIC COOPERATIVE CORPORATION | West Liberty | — | $38.7M | 15 |
| LOUISVILLE ARENA AUTHORITY INC | Louisville | N70 Recreation & Sports | $38.4M | 0 |
| MIDWAY UNIVERSITY INC FKA MIDWAY COLLEGE | Midway | B41Z Education | $38.1M | 12 |
| KENTUCKY MOUNTAIN HEALTH ALLIANCE I | Hazard | E32 Health Care | $37.3M | 5 |
| EMHFL INC | Danville | E22 Health Care | $37M | 18 |
| U OF L HEALTH - SHELBYVILLE INC | Louisville | E22 Health Care | $36.9M | 15 |
| KENTUCKY BLOOD CENTER INC | Lexington | E61Z Health Care | $36.9M | 8 |
| 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 |
| LOUISVILLE COLLEGIATE SCHOOL | Louisville | B200 Education | $36.3M | 6 |
| NORTHERN KENTUCKY AREA DEVELOPMENT DISTRICT | Florence | S32 Community Improvement & Capacity Building | $36.2M | 1 |
| KENTUCKY HOSPITAL ASSOCIATION | Louisville | — | $35.7M | 33 |
| MOUNTAIN RURAL TELEPHONE COOPERATIVE CORPORATION | West Liberty | — | $34.4M | 12 |
| UNION COMMONWEALTH UNIVERSITY | Barbourville | B430 Education | $34.4M | 12 |
| BRECKINRIDGE HEALTH INC | Hardinsburg | E22Z Health Care | $34.3M | 7 |
| CALDWELL COUNTY HOSPITAL INC CALDWELL MEDICAL CENTER | Princeton | E22Z Health Care | $33.8M | 6 |
| KENTUCKY WESLEYAN COLLEGE | Owensboro | B420 Education | $33.7M | 9 |
| FOOTHILLS RURAL TELEPHONE COOPERATIVE | Staffordsville | — | $33.7M | 11 |
| UNITED STATES CATHOLIC CONFERENCE NAZARETH HOME INC | Louisville | — | $32.8M | 7 |
| Christian Academy of Louisville Inc | Louisville | B20 Education | $32.7M | 6 |
| Association Healthcare Consortium Inc dba KBA Benefits Trust | Louisville | Y43 Mutual & Membership Benefit | $32.5M | 0 |
| BOYS & GIRLS CLUB WORKERS ASSOCIATION | Lexington | — | $32.4M | 0 |
| THE CHILDREN'S HOSPITAL FOUNDATION INC | Louisville | E110 Health Care | $32.1M | 12 |
| AMERICAN BOARD OF FAMILY MEDICINE INC | Lexington | — | $31.9M | 29 |
| Healthpoint Family Care Inc | Newport | E30Z Health Care | $31.8M | 8 |
| WKU STUDENT LIFE FOUNDATION INC | Bowling Green | B110 Education | $31.5M | 1 |
| MEMBERS HERITAGE CREDIT UNION INC | Lexington | — | $31.4M | 6 |
| KENTON HOUSING INC | Latonia | L22Z Housing & Shelter | $30.9M | 9 |
| Transcend Credit Union | Louisville | — | $30.8M | 9 |
| 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 |
| CCMH CORPORATION | Carrollton | E21 Health Care | $29.9M | 6 |
| HealthFirst Bluegrass Inc | Lexington | E32 Health Care | $29.3M | 9 |
| KENTUCKY LABORERS DISTRICT COUNCIL HEALTH & WELFARE FUND | Lawrenceburg | — | $28.9M | 1 |
| MARSHALL COUNTY HOSPITAL DISTRICT | Benton | E220 Health Care | $28.8M | 7 |
| MATTHEW 25 AIDS SERVICES INC | Henderson | E600 Health Care | $28.5M | 1 |
| LIVINGSTON HOSPITAL & HEALTHCARE SERVICES INC | Salem | E220 Health Care | $28.4M | 6 |
| BIG SANDY RURAL ELECTRIC COOPERATIVE CORPORATION | Paintsville | — | $27.8M | 15 |
| PARK DUVALLE COMMUNITY HEALTH CENTER INC | Louisville | — | $27.8M | 13 |
| EAST CENTRAL ILLINOIS PIPETRADES HEALTH & WELFARE PLAN | Lexington | — | $27.1M | 0 |
| BLUE GRASS COMMUNITY ACTION PARTNERSHIP INC | Frankfort | P20Z Human Services | $27M | 1 |
| RAY & KAY ECKSTEIN CHARITABLE TRUST | Paducah | B82 Education | $26.9M | 0 |
| CHRISTIAN CARE COMMUNITIES INC GROUP RETURN | Louisville | P750 Human Services | $26.9M | 9 |
