| THE HOME OF THE INNOCENTS INC | Louisville | P300 Human Services | $61.4M | 9 |
| Family Health Centers Inc | Louisville | E20 Health Care | $60.8M | 8 |
| FEDERATED TRANSPORTATION SERVICES | Lexington | P52Z Human Services | $60.8M | 0 |
| COMMUNICARE INC | Elizabethtown | F330 Mental Health & Crisis Intervention | $60.8M | 7 |
| CUMBERLAND VALLEY ELECTRIC INC | Gray | — | $60.2M | 12 |
| DARE TO CARE INC | Louisville | K31Z Food, Agriculture & Nutrition | $59.4M | 7 |
| AUDUBON AREA COMMUNITY SERVICES INC | Owensboro | P200 Human Services | $59.3M | 4 |
| CLARK ENERGY COOPERATIVE CORPORATION | Winchester | — | $58.9M | 16 |
| COMMUNITY ACT COUNCIL FOR LEX-FAY BOUR HARR AND NICH COUNTIES INC | Lexington | B22Z Education | $58.2M | 7 |
| THOMAS MORE UNIVERSITY INC | Crestview Hills | B420 Education | $57.6M | 9 |
| ELECTRICAL WORKERS LOCAL 369 BENEFIT FUND | Louisville | — | $57.5M | 0 |
| KENTUCKY RIVER COMMUNITY CARE INC | Hazard | F300 Mental Health & Crisis Intervention | $57.3M | 0 |
| the Young Men's Christian Association of Greater Louisville Inc | Louisville | P270 Human Services | $57.2M | 8 |
| THE FISCHER FAMILY FOUNDATION 2008 | Fort Mitchell | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $57.1M | 0 |
| LEXINGTON CENTER CORPORATION | Lexington | S20 Community Improvement & Capacity Building | $56.8M | 0 |
| SHELBY ENERGY COOPERATIVE | Shelbyville | — | $56.4M | 12 |
| SMITH BROTHERS FAMILY FOUNDATION INC | Louisville | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $56.3M | 0 |
| KENTUCKY CONSTRUCTION INDUSTRY HEALTH TR | Lexington | Y43 Mutual & Membership Benefit | $54.8M | 0 |
| IUOE LOCALS 181 320 AND TVA H&W TRUST FUND | Henderson | — | $53.1M | 0 |
| LESLIE KNOTT LETCHER PERRY COMMUNITY ACTION COUNCIL INC | Hazard | — | $52.3M | 3 |
| LAKE CUMBERLAND REGIONAL MH-MR BOARD INC | Somerset | F300 Mental Health & Crisis Intervention | $51.8M | 4 |
| RIVERVALLEY BEHAVIORAL HEALTH INC | Owensboro | F320 Mental Health & Crisis Intervention | $51.8M | 1 |
| BREEDERS' CUP LIMITED | Lexington | — | $51.5M | 11 |
| HORSERACING INTEGRITY AND SAFETY AUTHORITY INC | Lexington | S41 Community Improvement & Capacity Building | $50.6M | 7 |
| SOUTHEASTERN KENTUCKY REHABILITATION INDUSTRIES INC | Corbin | E50Z Health Care | $50.5M | 5 |
| Norton WLH Real Estate Inc | Louisville | E80 Health Care | $50.3M | 0 |
| FRONTIER NURSING UNIVERSITY INC | Versailles | B55Z Education | $50.1M | 10 |
| RUSSELL COUNTY KENTUCKY HOSPITAL DISTRICT HEALTH FACILITIES CORP | Russell Springs | E22Z Health Care | $49.8M | 9 |
| PATHWAYS INC | Ashland | F30Z Mental Health & Crisis Intervention | $49.6M | 5 |
| INDUSTRIAL MANUFACTURING AND PROFESSIONAL COMMERCIAL TRUST | Lexington | — | $48.7M | 1 |
| COLLEGE HEIGHTS FOUNDATION INC | Bowling Green | B110 Education | $48.2M | 6 |
| NORTHERN KENTUCKY MHMR REGIONAL BOARD INC | Covington | F300 Mental Health & Crisis Intervention | $47.7M | 8 |
| BIG SANDY HEALTH CARE INC | Prestonsburg | — | $47.2M | 8 |
| SPALDING UNIVERSITY INC | Louisville | B42Z Education | $47.1M | 11 |
| HEALTH HELP INC | Richmond | — | $46.7M | 11 |
| Partners for Rural Impact Inc | Berea | B90 Education | $46.1M | 11 |
| ASBURY THEOLOGICAL SEMINARY | Wilmore | B500 Education | $45.3M | 8 |
| BLUE GRASS COMMUNITY FOUNDATION INC | Lexington | T31Z Philanthropy, Voluntarism & Grantmaking Foundations | $45.1M | 3 |
| James B Haggin Memorial Hospital Inc | Harrodsburg | E22Z Health Care | $45M | 21 |
| Faith Healthcare Inc | Somerset | P80 Human Services | $44.7M | 15 |
| NATIONAL ASSOCIATION OF STATE PROCUREMENT OFFICALS INC | Lexington | B99Z Education | $44M | 14 |
| GO-HIRE EMPLOYMENT AND DEVELOPMENT INC | Hazard | J20 Employment | $44M | 7 |
| MASONIC HOMES OF KENTUCKY INC | Masonic Home | P750 Human Services | $42.7M | 7 |
| THE RAWLINGS FOUNDATION INC | LaGrange | T23 Philanthropy, Voluntarism & Grantmaking Foundations | $42.4M | 9 |
| Baptist Health Deaconess Medical Group | Madisonville | E30 Health Care | $40.7M | 6 |
| CUMBERLAND RIVER BEHAVIORAL HEALTH INC | Corbin | F30Z Mental Health & Crisis Intervention | $40.7M | 11 |
| CHRISTIAN CARE COMMUNITIES INC | Louisville | — | $40.5M | 8 |
| STERLING HEALTH SOLUTIONS INC | Mt Sterling | E20 Health Care | $40.2M | 10 |
| KENTUCKY LIFE AND HEALTH INSURANCE GUARANTY ASSOCIATION | Prospect | — | $40.1M | 1 |
| GRAYSON RURAL ELECTRIC COOPERATIVE CORPORATION | Grayson | — | $40.1M | 13 |
