| the Young Men's Christian Association of Greater Louisville Inc | Louisville | P270 Human Services | $57.2M | 8 |
| BLUE GRASS COMMUNITY FOUNDATION INC | Lexington | T31Z Philanthropy, Voluntarism & Grantmaking Foundations | $57.2M | 2 |
| TAYLOR COUNTY RURAL ELECTRIC | Campbellsville | — | $57M | 15 |
| FEDERATED TRANSPORTATION SERVICES | Lexington | P52Z Human Services | $57M | 0 |
| LEXINGTON CENTER CORPORATION | Lexington | S20 Community Improvement & Capacity Building | $56.8M | 0 |
| SMITH BROTHERS FAMILY FOUNDATION INC | Louisville | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $56.3M | 0 |
| KENTUCKY RIVER COMMUNITY CARE INC | Hazard | F300 Mental Health & Crisis Intervention | $55.4M | 0 |
| KENTUCKY CONSTRUCTION INDUSTRY HEALTH TR | Lexington | Y43 Mutual & Membership Benefit | $54.8M | 0 |
| DARE TO CARE INC | Louisville | K31Z Food, Agriculture & Nutrition | $53.9M | 8 |
| SHELBY ENERGY COOPERATIVE | Shelbyville | — | $53.5M | 12 |
| IUOE LOCALS 181 320 AND TVA H&W | Henderson | — | $53.1M | 0 |
| UNIVERSITY OF LOUISVILLE FOUNDATION | Louisville | B110 Education | $52.8M | 3 |
| LESLIE KNOTT LETCHER PERRY COMMUNITY | Hazard | — | $52.3M | 3 |
| RIVERVALLEY BEHAVIORAL HEALTH INC | Owensboro | F320 Mental Health & Crisis Intervention | $51.8M | 1 |
| BREEDERS' CUP LIMITED | Lexington | — | $51.5M | 11 |
| HORSERACING INTEGRITY AND SAFETY | Lexington | S41 Community Improvement & Capacity Building | $50.6M | 7 |
| SOUTHEASTERN KENTUCKY REHABILITATION | Corbin | E50Z Health Care | $50.5M | 5 |
| NORTHERN KENTUCKY MHMR REGIONAL BOARD | Covington | F300 Mental Health & Crisis Intervention | $50M | 8 |
| PATHWAYS INC | Ashland | F30Z Mental Health & Crisis Intervention | $49.6M | 5 |
| NORTON HEALTHCARE-INDIANA INC | Louisville | E20 Health Care | $49M | 4 |
| INDUSTRIAL MANUFACTURING AND | Lexington | — | $48.7M | 1 |
| COLLEGE HEIGHTS FOUNDATION INC | Bowling Green | B110 Education | $48.2M | 6 |
| Family Health Centers Inc | Louisville | E20 Health Care | $47.7M | 9 |
| BIG SANDY HEALTH CARE INC | Prestonsburg | — | $47.2M | 8 |
| ENA INC | Lexington | P320 Human Services | $47.2M | 0 |
| FRONTIER NURSING UNIVERSITY INC | Versailles | B55Z Education | $46.9M | 8 |
| HEALTH HELP INC | Richmond | — | $46.7M | 11 |
| LAKE CUMBERLAND REGIONAL MH-MR BOARD INC | Somerset | F300 Mental Health & Crisis Intervention | $46.7M | 4 |
| Faith Healthcare Inc | Somerset | P80 Human Services | $44.7M | 15 |
| CASEY COUNTY HOSPITAL DISTRICT | Liberty | — | $44.2M | 0 |
| NATIONAL ASSOCIATION OF STATE | Lexington | B99Z Education | $44M | 14 |
| GO-HIRE EMPLOYMENT AND DEVELOPMENT | Hazard | J20 Employment | $44M | 7 |
| SPALDING UNIVERSITY INC | Louisville | B42Z Education | $43.4M | 11 |
| JANE TODD CRAWFORD MEMORIAL HOSP | Greensburg | E20 Health Care | $42.4M | 0 |
| THE RAWLINGS FOUNDATION INC | LaGrange | T23 Philanthropy, Voluntarism & Grantmaking Foundations | $42.4M | 9 |
| Answers In Genesis Inc | Petersburg | X20Z Religion-Related | $42.1M | 10 |
| MASONIC HOMES OF KENTUCKY INC | Masonic Home | P750 Human Services | $41.6M | 7 |
| CENTRAL KENTUCKY MANAGEMENT SERVICES INC | Lexington | E8XZ Health Care | $41.1M | 11 |
| GRAYSON RURAL ELECTRIC | Grayson | — | $41.1M | 11 |
| Baptist Health Deaconess Medical Group | Madisonville | E30 Health Care | $40.7M | 6 |
| CHRISTIAN CARE COMMUNITIES INC | Louisville | — | $40.5M | 8 |
| ELECTRICAL WORKERS LOCAL 369 | Louisville | — | $40.4M | 0 |
| CUMBERLAND RIVER BEHAVIORAL HEALTH INC | Corbin | F30Z Mental Health & Crisis Intervention | $40.3M | 11 |
| STERLING HEALTH SOLUTIONS INC | Mt Sterling | E20 Health Care | $40.2M | 10 |
| RUSSELL COUNTY KENTUCKY HOSPITAL | Russell Springs | E22Z Health Care | $40.1M | 8 |
| AMERICAN PRINTING HOUSE | Louisville | A330 Arts, Culture & Humanities | $39.4M | 13 |
| THE MEDICAL CENTER AT FRANKLIN INC | Bowling Green | E220 Health Care | $38.9M | 12 |
| UNIVERSITY OF LOUISVILLE REAL ESTATE | Louisville | T30 Philanthropy, Voluntarism & Grantmaking Foundations | $38.5M | 1 |
| LOUISVILLE ARENA AUTHORITY INC | Louisville | N70 Recreation & Sports | $38.4M | 0 |
| MIDWAY UNIVERSITY INC | Midway | B41Z Education | $38.1M | 12 |
