| 1 | Saint Joseph Health System INC | Health Care | $1.0B | $704.5M |
| 2 | Appalachian Regional Healthcare INC | Health Care | $943.9M | $1.4B |
| 3 | University of Kentucky Research Foundation | Education | $493.2M | $265.5M |
| 4 | Kentucky Medical Services Foundation INC | Education | $386.2M | $224.7M |
| 5 | Arh Tug Valley Health Services INC | Health Care | $217.9M | $116.5M |
| 6 | Hospice of the Bluegrass INC | Human Services | $158.4M | $126.3M |
| 7 | Arh Mary Breckinridge Health Services INC | Health Care | $128.3M | $172.5M |
| 8 | New Vista of the Bluegrass INC | Mental Health & Crisis Intervention | $122.1M | $68.1M |
| 9 | Lexington Cemetery Company | Unclassified | $119.1M | $160.0M |
| 10 | New Vista Communities INC | Mental Health & Crisis Intervention | $119.0M | $24.7M |
| 11 | National Association of State Procurement Officials | Education | $87.5M | $178.1M |
| 12 | Blue Grass Community Foundation INC | Philanthropy, Voluntarism & Grantmaking | $87.4M | $253.0M |
| 13 | American Eagle Lifecare Corporation | Health Care | $84.9M | $258.7M |
| 14 | American Board of Family Medicine INC | Unclassified | $79.4M | $187.4M |
| 15 | New Vista Behavioral Healthcare INC | Mental Health & Crisis Intervention | $78.6M | $12.3M |
| 16 | Gods Pantry Food Bank INC | Unclassified | $78.3M | $34.6M |
| 17 | Community Action Council for Lex- Fayette Bourb Harr Nich Counties | Education | $70.0M | $42.6M |
| 18 | Council of State Governments | Unclassified | $65.5M | $76.9M |
| 19 | Federated Transportation Services of the Bluegrass INC | Human Services | $60.8M | $48.9M |
| 20 | Lexington Center Corporation | Community Improvement & Capacity Building | $56.8M | $357.5M |
| 21 | Construction Industry Health & Welfare Trust Fund | Unclassified | $56.1M | $15.4M |
| 22 | Kentucky Construction Industry Health Tr | Mutual & Membership Benefit | $55.7M | $1.8M |
| 23 | Breeders Cup Limited | Unclassified | $54.8M | $123.7M |
| 24 | Industrial Manufacturing Professional and Commercial Trust | Unclassified | $54.3M | $9.3M |
| 25 | Horseracing Integrity and Safety Authority INC | Community Improvement & Capacity Building | $50.6M | $15.8M |
| 26 | Lexington School INC | Education | $47.8M | $84.2M |
| 27 | Abfm Foundation INC | Human Services | $45.4M | $130.6M |
| 28 | United States Equestrian Federation INC | Recreation & Sports | $39.9M | $38.1M |
| 29 | Central Kentucky Management Services INC | Health Care | $39.6M | $2.9M |
| 30 | United Steelworkers of America Afl-cio Health & Welfare Fund | Unclassified | $37.1M | $11.6M |
| 31 | Kentucky Blood Center INC | Health Care | $37.1M | $51.1M |
| 32 | William Lawrence & Blanche Hughes Foundation | Philanthropy, Voluntarism & Grantmaking | $35.5M | $184.1M |
| 33 | Kentucky Easter Seal Society INC | Health Care | $33.7M | $100.7M |
| 34 | Healthfirst Bluegrass INC | Health Care | $31.1M | $35.5M |
| 35 | Employment Solutions INC | Employment | $30.8M | $20.8M |
| 36 | IBEW Local 150 Welfare Fund | Unclassified | $28.9M | $47.6M |
| 37 | Phi Gamma Delta Educational Foundation | Unclassified | $28.6M | $34.0M |
| 38 | Construction Industry of Kansas Health & Welfare Trust Fund Agreem | Unclassified | $27.6M | $6.0M |
| 39 | Sayre Christian Village Nursing Home INC | Health Care | $25.3M | $16.2M |
| 40 | Lexington Public Library | Education | $24.7M | $68.8M |
| 41 | Commonwealth Fund for Ket INC | Arts, Culture & Humanities | $24.1M | $50.2M |
| 42 | YMCA of Central Ky | Unclassified | $21.9M | $48.7M |
| 43 | Lexington Christian Academy INC | Education | $20.1M | $43.3M |
| 44 | University of Kentucky Alumni Association INC | Education | $19.7M | $28.9M |
| 45 | Sayre School | Education | $18.7M | $34.8M |
| 46 | Kentucky Educational Television Foundation INC | Arts, Culture & Humanities | $17.1M | $17.9M |
| 47 | Clean Streams Foundation INC | Environment | $16.7M | $221.6M |
| 48 | Continuing Care Hospital INC | Unclassified | $15.7M | $15.7M |
| 49 | James a and Martha R Brown Charitable Foundation INC | Philanthropy, Voluntarism & Grantmaking | $14.9M | $38.6M |
| 50 | International Coach Federation INC | Unclassified | $14.0M | $19.2M |
| 51 | Hope Center INC | Housing & Shelter | $13.4M | $20.0M |
| 52 | Community Ventures Corporation INC | Community Improvement & Capacity Building | $12.8M | $100.3M |
| 53 | International Coaching Federation Global Enterprise | Community Improvement & Capacity Building | $12.8M | $22.6M |
| 54 | National Thoroughbred Racing | Unclassified | $12.6M | $18.6M |
| 55 | Bluegrass Primary Health Care Center INC | Health Care | $12.5M | $8.7M |
| 56 | Kentucky Primary Care Association Health and Benefits Tr | Mutual & Membership Benefit | $12.3M | $440K |
| 57 | Impact Energy Industry Health Trust | Employment | $12.1M | $331K |
| 58 | Kentucky 4-H Foundation INC | Youth Development | $11.8M | $11.8M |
| 59 | Kentucky Cattlemens Foundation INC | Education | $11.4M | $12.4M |
| 60 | Kentuckyone Health INC | Health Care | $11.4M | $11.3M |
| 61 | Asphalt Institute INC | Unclassified | $11.2M | $14.8M |
| 62 | Kentucky Nonprofit Network Group Insurance Trust | Mutual & Membership Benefit | $10.4M | $55K |
| 63 | Childrens Advocacy Centers of Kentucky INC | Crime & Legal-Related | $9.9M | $2.5M |
| 64 | United States Hunter Jumper Association INC | Recreation & Sports | $9.9M | $20.7M |
| 65 | Goodenough Collaboration Trust | Unclassified | $9.8M | $5.2M |
| 66 | E O Robinson Mountain Fund | Unclassified | $9.6M | $19.8M |
| 67 | Pisacano Leadership Foundation INC | Education | $9.2M | $13.7M |
| 68 | Prichard Committee for Academic Excellence | Education | $9.2M | $7.0M |
| 69 | New Vocation Racehorse Adoption Program | Animal-Related | $9.1M | $9.9M |
| 70 | Bargaining Association Steelworkers Local 14614 Health and Welfare Fun | Unclassified | $9.1M | $5.3M |
| 71 | Idle Hour Country Club INC | Recreation & Sports | $9.1M | $17.7M |
| 72 | Equestrian Events INC | Unclassified | $8.8M | $2.1M |
| 73 | Key Assets Kentucky INC | Mental Health & Crisis Intervention | $8.7M | $3.0M |
| 74 | Kentucky Cattlemens Assoc | Unclassified | $8.6M | $5.9M |
| 75 | Lexington Country Club INC | Unclassified | $8.2M | $12.3M |
| 76 | Jobs for Kentuckys Graduates INC | Education | $7.9M | $6.6M |
| 77 | Plumbers & Steamfitters Local 577 Health and Welfare Fund | Unclassified | $7.9M | $4.2M |
| 78 | American Association of Equine Practitioners | Unclassified | $7.8M | $9.8M |
| 79 | Plumbers & Steamfitters Local Union 452 Health & Welfare Tr Fund | Unclassified | $7.7M | $4.8M |
| 80 | Voices of Hope Lexington INC | Mental Health & Crisis Intervention | $7.5M | $4.5M |
| 81 | Lexington Humane Society | Animal-Related | $7.5M | $9.8M |
| 82 | Icf Credentialing and Standards | Community Improvement & Capacity Building | $7.5M | $1.7M |
| 83 | Kentucky Science and Technology Corporation | Unclassified | $7.2M | $23.7M |
| 84 | Kentucky High School Athletic Association | Recreation & Sports | $7.2M | $7.7M |
| 85 | National Association of State Chief Information Officers INC | Unclassified | $7.2M | $6.5M |
| 86 | Ronald McDonald House Charities of the Bluegrass INC | Diseases, Disorders & Medical Disciplines | $7.1M | $7.3M |
| 87 | International Brotherhood of Electrical Workers | Unclassified | $7.1M | $2.0M |
| 88 | Plumbers & Steamfitters Local Union #248 Health & Welfare Trust Fund | Unclassified | $7.0M | $10.0M |
| 89 | Girl Scouts of Kentuckys Wilderness Road Council INC | Unclassified | $7.0M | $10.4M |
| 90 | The Susan S Donaldson Foundation INC | Unclassified | $6.9M | $37.8M |
| 91 | Thoroughbred Aftercare Alliance Foundation INC | Animal-Related | $6.7M | $8.5M |
| 92 | American Legion | Unclassified | $6.7M | $780K |
| 93 | Generous Giving INC | Religion-Related | $6.4M | $5.0M |
| 94 | Sayre Village Phase III INC | Housing & Shelter | $6.2M | $16.0M |
| 95 | United States Dressage Federation INC | Unclassified | $6.2M | $11.7M |
| 96 | Elhapa Foundation INC | Philanthropy, Voluntarism & Grantmaking | $6.1M | $35.6M |
| 97 | Greater Kentucky Credit Union INC | Unclassified | $5.7M | $89.9M |
| 98 | Child Development Centers of the Bluegrass INC | Human Services | $5.7M | $9.6M |
| 99 | Dr Marius E Johnston and Margaret Johnston Wright Memorial Trust | Unclassified | $5.7M | $14.6M |
| 100 | Phi Gamma Delta Fraternity | Unclassified | $5.6M | $16.5M |