| Date Filed | Type | Ordinance | Map Status | Notes |
| 2024-10-03 | Annexation (TIFF) (PDF) | 2024-03 | MAPPABLE | Tract located west of the City of Madisonville. Total Acres: 429.265 |
| 2021-03-15 | Annexation (TIFF) (PDF) | 2021-3 aka O-2021-3 | MAPPABLE | Devaditi Tract located at 2015 Grapevine Road: 0.7611 acres |
| 2020-05-21 | Population Estimate | | | U. S. Census Bureau Population Estimate as of July 1, 2019: 18,621 |
| 2020-03-20 | Notification of Appointment (TIFF) (PDF) | | | Chad Menser was appointed to the City Council to fill the vacancy created by the passing of Council Member Bobby Johnson. |
| 2020-03-05 | Notification of Vacancy (TIFF) (PDF) | | | Vacancy due to the death of City Council Member Bobby Johnson. |
| 2019-12-17 | Annexation (TIFF) (PDF) | 1990-10-19 | MAPPABLE | Duplicate Filing. Tract located along and west of Edward T. Breathitt Pennyrile Parkway: 1042.018 acres |
| 2019-12-17 | Resolution (TIFF) (PDF) | 2019-60 | MAPPABLE | Restates the location of Annexation Ordinance 1990-10-19 |
| 2019-12-17 | Resolution (TIFF) (PDF) | 2019-59 | MAPPABLE | Rescinds Resolution 2016-14 filed with the Office of Secretary of State on April 5, 2018. |
| 2019-12-11 | Annexation (TIFF) (PDF) | 2019-11 | MAPPABLE | Markham Tract known as Lot No. 5, Oakwood Hills Subdivision along Buffalo Trace: 8.44 acres |
| 2019-05-23 | Population Estimate | | | U. S. Census Bureau Population Estimate as of July 1, 2018: 18,833 |
| 2018-05-24 | Population Estimate | | | U. S. Census Bureau Population Estimate as of July 1, 2017: 19,067 |
| 2018-04-05 | Annexation (TIFF) (PDF) | 1990-10-19 | MAPPABLE | Tract located along and west of Edward T. Breathitt Pennyrile Parkway: 1007.400 acres |
| 2018-04-05 | Resolution (TIFF) (PDF) | 2016-14 | MAPPABLE | Restates the location of Annexation Ordinance 1990-10-19 |
| 2016-05-19 | Population Estimate | | | U. S. Census Bureau Population Estimate as of July 1, 2015: 19,539 |
| 2015-05-21 | Population (2010) | | | Population Total per 2010 U.S. Decennial Census: 19,591 |
| 2014-07-24 | Declaration (TIFF) (PDF) | pursuant to HB 331 (2014) | | Acknowledgment of Reclassification (Home Rule), Statement of Form of Government (Mayor-Council), Name of City, & Year of Incorporation |
| 2010-12-17 | Annexation (TIFF) (PDF) | Civil Action 2499 dated December 22, 1977 | MAPPABLE | Tract located in the Cross Creek area: 54.84 acres |
| 2010-12-17 | Resolution (TIFF) (PDF) | 2010-11 | MAPPABLE | Depicts and describes Annexation Ordinance styled Civil Action No. 2499, dated Dec 22, 1977 |
| 2010-01-15 | Resolution (TIFF) (PDF) | 2010-2 | MAPPABLE | Depicts and describes Annexation Ordinance dated April 7, 1969. |
| 2010-01-15 | Resolution (TIFF) (PDF) | 2010-3 | MAPPABLE | Depicts and describes Annexation Ordinance styled Civil Action No. 78-CI-537. |
| 2010-01-15 | Resolution (TIFF) (PDF) | 2010-1 | MAPPABLE | Restates location of Annexation Ordinance 05-04 |
| 2009-12-30 | Annexation (TIFF) (PDF) | dated April 7, 1969 | MAPPABLE | Corrects KRS 81.045 filing submitted in 1981 by adding tracts annexed Apr 7, 1969. |
| 2009-12-30 | Annexation (TIFF) (PDF) | Civil Action 78-CI-537 dated October 2, 1978 | MAPPABLE | Corrects KRS 81.045 filing submitted in 1981 by adding Annexation styled Civil Action No. 78-CI-537. |
| 2009-12-30 | Annexation (TIFF) (PDF) | 05-04 | MAPPABLE | Woodgate Subdivision: northeast corner of Brown Rd & Gill Field Rd (21.357a) |
| 2009-01-05 | Notification of Vacancy (TIFF) (PDF) | | | Fifth District Magistrate |
| 2008-10-31 | Annexation | Brooks Tract III-A | MAPPABLE | 990.19 acres |
| 2008-10-31 | Resolution (TIFF) (PDF) | 2008-09 | MAPPABLE | Restates location for Brooks Tract III-A annexation |
| 2008-02-12 | Governor's Appointment (TIFF) (PDF) | Executive Order #2008-0149 | | Property Valuation Administrator |
| 2007-04-20 | Annexation (TIFF) (PDF) | 07-06 | MAPPABLE | City of Madisonville Tract: Grapevine Lake & surrounding area (188.19 acres) |
| 2006-03-27 | Annexation (TIFF) (PDF) | 06-04 | MAPPABLE | Davis, Winstead & Fox Tract: Oakwood Lane to Tucker Schoolhouse Rd (35.100 acres) |
| 2005-01-18 | Annexation (TIFF) (PDF) | 04-22 | MAPPABLE | The Courses-The Backside Phase 3: 17.43 acres |
| 2004-11-08 | Annexation (TIFF) (PDF) | 98-13 | MAPPABLE | |
| 2000-12-14 | Annexation (TIFF) (PDF) | 99-18 | MAPPABLE | |
| 2000-12-14 | Annexation (TIFF) (PDF) | 20-18 | MAPPABLE | |
| 1998-12-09 | Annexation (TIFF) (PDF) | 98-22 | MAPPABLE | |
| 1998-11-16 | Annexation (TIFF) (PDF) | 98-18 | MAPPABLE | |
| 1996-06-24 | Annexation (TIFF) (PDF) | 96-28 | MAPPABLE | |
| 1996-01-02 | Annexation (TIFF) (PDF) | 95-24 | MAPPABLE | |
| 1996-01-02 | Annexation (TIFF) (PDF) | 95-21 | MAPPABLE | |
| 1996-01-02 | Annexation (TIFF) (PDF) | 95-20 | MAPPABLE | |
| 1995-08-18 | Annexation (TIFF) (PDF) | 95-05 | MAPPABLE | |
| 1994-10-07 | Governor's Appointment (TIFF) (PDF) | Executive Order #94-1035 | | City Council Member |
| 1994-05-27 | Annexation (TIFF) (PDF) | 94-09 | MAPPABLE | |
| 1993-11-18 | Census (TIFF) (PDF) | | | Population: 18,693 (Dec.24, 1991) |
| 1993-08-06 | Annexation (TIFF) (PDF) | 93-20 | MAPPABLE | |
| 1993-06-25 | Annexation (TIFF) (PDF) | Legion Drive | MAPPABLE | |
| 1993-05-10 | Annexation (TIFF) (PDF) | 93-08 | MAPPABLE | |
| 1992-09-28 | Census (TIFF) (PDF) | | | Population: 16,203 (1990) |
| 1992-08-21 | Annexation (TIFF) (PDF) | McLeod Lane | MAPPABLE | |
| 1992-05-29 | Annexation (TIFF) (PDF) | Country Club Estates | MAPPABLE | |
| 1992-03-16 | Annexation (TIFF) (PDF) | Moose Lodge | MAPPABLE | |
| 1992-03-03 | Annexation (TIFF) (PDF) | Brown Road | MAPPABLE | |
| 1992-03-03 | Annexation (TIFF) (PDF) | Anton Road | MAPPABLE | |
| 1991-01-17 | Annexation (TIFF) (PDF) | Ridgewood Sub., Ruby, & Brooks | MAPPABLE | Three Tracts |
| 1990-10-19 | Annexation (TIFF) (PDF) | Big Springs Inn Property | MAPPABLE | |
| 1990-10-19 | Annexation (TIFF) (PDF) | Tom Reynolds Road | MAPPABLE | County High School Tract located along Highway 1069. |
| 1990-10-19 | Annexation (TIFF) (PDF) | Tucker Schoolhouse Road | MAPPABLE | Tract contains 33 acres. |
| 1989-05-01 | Annexation (TIFF) (PDF) | High School Property | MAPPABLE | |
| 1989-05-01 | Annexation (TIFF) (PDF) | Portion of Ridgewood Subdivision | MAPPABLE | |
| 1989-05-01 | Annexation (TIFF) (PDF) | McGaw Property (2 Tracts) | MAPPABLE | |
| 1989-05-01 | Annexation (TIFF) (PDF) | nr Madisonville Community College | MAPPABLE | |
| 1989-05-01 | Annexation (TIFF) (PDF) | Church Lot, Wiman, Moose Club Lane | MAPPABLE | |
| 1989-05-01 | Annexation (TIFF) (PDF) | Main St. & McLeod Lane | MAPPABLE | |
| 1989-05-01 | Annexation (TIFF) (PDF) | nr Elk Creek | MAPPABLE | |
| 1989-05-01 | Annexation (TIFF) (PDF) | along L & N Railroad | MAPPABLE | |
| 1989-05-01 | Annexation (TIFF) (PDF) | Midway Avenue & Dozier Heights Add. | MAPPABLE | |
| 1981-05-11 | KRS 81.045 Filing (TIFF) (PDF) | | MAPPABLE | |