| 1 | East Kentucky Power Cooperative INC Winchester | $1.2B | $1.2B | $3.9B |
| 2 | Kenergy Corp. Henderson | $376.6M | $376.4M | $393.5M |
| 3 | Warren Rural Electric Cooperative Corporation Bowling Green | $268.7M | $268.7M | $393.8M |
| 4 | Owen Electric Cooperative INC Owenton | $246.5M | $246.5M | $319.2M |
| 5 | Disabled American Veterans Erlanger | $238.9M | $176.5M | $654.7M |
| 6 | Delta Dental of Kentucky INC Louisville | $217.1M | $196.4M | $140.0M |
| 7 | Gheens Foundation INC Louisville | $201.1M | $0 | $158.8M |
| 8 | Pennyrile Rural Electric Cooperative Corporation Hopkinsville | $168.6M | $168.6M | $312.8M |
| 9 | South Kentucky Rural Electric Cooperative Corp. Somerset | $156.5M | $156.5M | $355.1M |
| 10 | Salt River Electric Cooperative Corporation Bardstown | $137.8M | $137.8M | $221.0M |
| 11 | Jackson Energy Cooperative Corporat Ion INC McKee | $128.7M | $128.7M | $301.6M |
| 12 | Lexington Cemetery Company Lexington | $119.1M | $36.7M | $160.0M |
| 13 | Humana Foundation INC Louisville | $109.8M | $0 | $393.3M |
| 14 | West Kentucky Rural Electric Cooperative Corporation Mayfield | $109.8M | $109.8M | $193.1M |
| 15 | Flaget Healthcare INC Bardstown | $106.8M | $106.8M | $91.5M |
| 16 | Jackson Purchase Energy Corporation Paducah | $98.1M | $98.1M | $165.5M |
| 17 | Nolin Rural Electric Cooperative Corporation Elizabethtown | $94.7M | $94.7M | $168.3M |
| 18 | Fleming-mason Energy Cooperative INC Flemingsburg | $89.9M | $89.9M | $154.1M |
| 19 | Meade County Rural Electric Cooperative Corporation Brandenburg | $86.6M | $86.6M | $114.2M |
| 20 | Electrical Workers Local No 369 Benefit Fund Louisville | $82.7M | $57.5M | $112.3M |
| 21 | American Board of Family Medicine INC Lexington | $79.4M | $45.7M | $187.4M |
| 22 | Gods Pantry Food Bank INC Lexington | $78.3M | $78.1M | $34.6M |
| 23 | Inter-county Energy Cooperative Corporation Danville | $71.0M | $71.0M | $158.5M |
| 24 | Casey County Hospital District Liberty | $68.5M | $68.5M | $103.3M |
| 25 | Network for Hope INC Louisville | $67.9M | $61.5M | $57.8M |
| 26 | Farmers Rural Electric Cooperative Corporation Glasgow | $65.8M | $65.8M | $136.8M |
| 27 | Council of State Governments Lexington | $65.5M | $65.4M | $76.9M |
| 28 | Health Help Incorporated Richmond | $65.2M | $46.7M | $46.0M |
| 29 | Taylor County Rural Electric Cooperative Corporation Campbellsvlle | $62.9M | $62.8M | $114.6M |
| 30 | Cumberland Valley Electric Co-op Corp. Gray | $60.2M | $60.2M | $123.6M |
| 31 | Clark Energy Cooperative INC Winchester | $58.9M | $58.9M | $153.3M |
| 32 | Shelby Energy Cooperative INC Shelbyville | $56.4M | $56.4M | $148.2M |
| 33 | Construction Industry Health & Welfare Trust Fund Lexington | $56.1M | $25.5M | $15.4M |
| 34 | Breeders Cup Limited Lexington | $54.8M | $51.5M | $123.7M |
| 35 | Industrial Manufacturing Professional and Commercial Trust Lexington | $54.3M | $52.2M | $9.3M |
| 36 | Leslie Knott Letcher Perry Community Action Council Hazard | $52.4M | $52.3M | $31.9M |
| 37 | Kentucky Insurance Guaranty Association Louisville | $51.9M | $12.1M | $56.1M |
| 38 | International Union of Operating Engineers Local Unions 181 320 and Henderson | $50.5M | $50.5M | $96.8M |
| 39 | R C Durr Foundation INC Crescent Spgs | $47.7M | $0 | $86.2M |
| 40 | Big Sandy Health Care INC Prestonsburg | $47.2M | $47.2M | $41.2M |
| 41 | Whas Crusade for Children INC Louisville | $47.1M | $21.1M | $54.3M |
| 42 | Kentucky Laborers District Council Health and Welfare Fund Lawrenceburg | $46.4M | $28.9M | $46.2M |
| 43 | James Graham Brown Foundation INC Louisville | $45.4M | $0 | $391.0M |
| 44 | Christian Care Communities INC Louisville | $41.9M | $40.5M | $87.5M |
| 45 | Kentucky Life and Health Insurance Guaranty Association Prospect | $40.1M | $40.1M | $41.5M |
| 46 | Grayson Rural Electric Cooperative Corporation Grayson | $40.1M | $40.1M | $90.7M |
| 47 | Licking Valley Rural Electric Co-op Corporation West Liberty | $38.7M | $38.7M | $86.8M |
| 48 | Kentucky Hospital Association Louisville | $37.2M | $35.7M | $63.9M |
| 49 | United Steelworkers of America Afl-cio Health & Welfare Fund Lexington | $37.1M | $5.7M | $11.6M |
| 50 | Disabled American Veterans National Service Foundation Erlanger | $35.0M | $12.8M | $188.9M |