| Date Filed | Type | Ordinance | Map Status | Notes |
| 2025-12-15 | Annexation (TIFF) (PDF) | 11-2025 | IN PROGRESS | 2000 Boonesboro Road - 31.818 acres |
| 2025-12-08 | Annexation (TIFF) (PDF) | 12-2025 | IN PROGRESS | James Monroe - 2250 Boonesboro Road, Parcel 1 - 4.225 acres |
| 2025-09-15 | Annexation (TIFF) (PDF) | 10-2025 | UNMAPPABLE | Located on Colby Road 23.515 acres |
| 2024-09-27 | Annexation (TIFF) (PDF) | 12-2024 | MAPPABLE | Located on the north side of Frontier Way. (Clark County Board of Education): 12 acres. |
| 2024-02-28 | Annexation (TIFF) (PDF) | 1-2023 | MAPPABLE | Property located near the intersection of Frontier Way in Winchester, KY and being known as Oakmont Villas Unit 4-A: 6.5108 acres |
| 2022-02-07 | Annexation (TIFF) (PDF) | 10-2021 | MAPPABLE | Infiltrator Water Technologies, LLC, Tract located on the west side of Ky 627 (aka Paris Pike) & east of the CSX Railroad: 50 acres |
| 2020-06-24 | Annexation (TIFF) (PDF) | 3-2020 | MAPPABLE | Oakmont Villas, Unit 3-A, located along Gibson Way & Frontier Way: 6.421 acres |
| 2020-05-21 | Population Estimate | | | U. S. Census Bureau Population Estimate as of July 1, 2019: 18,548 |
| 2019-05-23 | Population Estimate | | | U. S. Census Bureau Population Estimate as of July 1, 2018: 18,577 |
| 2018-05-24 | Population Estimate | | | U. S. Census Bureau Population Estimate as of July 1, 2017: 18,486 |
| 2017-06-28 | Annexation (TIFF) (PDF) | 3-2017 | MAPPABLE | Infiltrator Water Technologies, Inc., Tract located on the west side of Ky 627 aka Paris Pike & east of the CSX Railroad: 70 acres |
| 2016-05-19 | Population Estimate | | | U. S. Census Bureau Population Estimate as of July 1, 2015: 18,446 |
| 2015-05-21 | Population (2010) | | | Population Total per 2010 U.S. Decennial Census: 18,368 |
| 2014-07-31 | Declaration (TIFF) (PDF) | pursuant to HB 331 (2014) | | Acknowledgment of Reclassification (Home Rule), Statement of Form of Government (City Manager), Name of City, & Year of Incorporation |
| 2014-02-13 | Annexation (TIFF) (PDF) | 16-2013 | MAPPABLE | Parcel A: Ky 627 - Boonesboro R/W (34.90 acres). Parcel B: George Rogers Clark High School, Ky 627 (89.15 acres). |
| 2014-02-04 | Annexation (TIFF) (PDF) | 12-2013 | MAPPABLE | Fairholme Ventures, LLC, Tract: south & east of Fairholme Way and west of Two Mile Road (44.430 acres) |
| 2012-09-20 | Annexation (TIFF) (PDF) | 6-2009 | MAPPABLE | Tract located on the south side of Cook Avenue: 0.884 acres |
| 2012-09-20 | Annexation Amendment (TIFF) (PDF) | 5-2010 | MAPPABLE | Corrects certain calls in Annexation Ordinance 6-2009 |
| 2012-05-22 | Annexation (TIFF) (PDF) | 4-2012 | MAPPABLE | Tract located along US 60, Caudill Drive, & Hospital Drive: 30.063 acres |
| 2010-09-20 | Annexation (TIFF) (PDF) | 1-87 | MAPPABLE | Annexation of areas addressed in Ord. 1-85 declared void by Circuit Court Action 85-CI-149. |
| 2010-09-20 | Resolution (TIFF) (PDF) | R2010-25 | MAPPABLE | Restates the location of Annexation Ordinance 1-87. (between I-64 & Lex Ave: 37.15a & 13.95a) |
| 2010-09-20 | Annexation (TIFF) (PDF) | 4-2008 | MAPPABLE | Tract located north of Revilo Rd & west of L & N Railroad: 31.32 acres |
| 2010-09-20 | Annexation (TIFF) (PDF) | 6-1998 | MAPPABLE | Earlymeade Farm & Earlymeade, LLC, Tract: Colby Rd & McClure Rd (134.46 acres) |
| 2010-09-20 | Resolution (TIFF) (PDF) | R2010-23 | MAPPABLE | Restates the location of Annexation Ordinance 6-1998 |
| 2010-09-20 | Resolution (TIFF) (PDF) | R2010-21 | MAPPABLE | Restates the location of Annexation Ordinance 4-2008 |
| 2010-09-20 | Annexation (TIFF) (PDF) | 21-2005 | MAPPABLE | Daniel Grove Cemetery: east Ky 974 aka Muddy Creek Road (8.45 acres) |
| 2010-09-20 | Resolution (TIFF) (PDF) | R2010-22 | MAPPABLE | Restates the location of Annexation Ordinance 21-2005 |
| 2010-06-17 | Annexation (TIFF) (PDF) | 11-1981 (aka 11-81) | MAPPABLE | Tract located north of I-64 between Old Paris Pike and L& N Railroad (104.67 acres) |
| 2010-06-17 | Resolution (TIFF) (PDF) | R2010-6 | MAPPABLE | Restates the location of Annexation Ordinance 11-1981 |
| 2010-06-17 | Annexation (TIFF) (PDF) | 10-1990 (aka 10-90) | MAPPABLE | Winchester-Clark County Industrial Development Authority Tract: adj Winchester Industrial Pk (2.54a) |
| 2010-06-17 | Resolution (TIFF) (PDF) | R2010-8 | MAPPABLE | Restates the location of Annexation Ordinance 10-1990 |
| 2010-06-17 | Annexation (TIFF) (PDF) | 10-2005 | MAPPABLE | Tract located along Van Meter Road: 317.24 acres |
| 2010-06-17 | Resolution (TIFF) (PDF) | R2010-10 | MAPPABLE | Restates the location of Annexation Ordinance 10-2005 |
| 2010-06-17 | Annexation (TIFF) (PDF) | 2-1988 (aka 2-88) | MAPPABLE | Tract located between Old Paris Pike and the L&N Railroad (118.48 acres) |
| 2010-06-17 | Resolution (TIFF) (PDF) | R2010-7 | MAPPABLE | Restates the location of Annexation Ordinance 2-1988 |
| 2008-07-23 | Notification of Vacancy (TIFF) (PDF) | | | Coroner |
| 2008-07-23 | County Judge's Appointment (TIFF) (PDF) | Executive Order #2008-09 | | Coroner |
| 2008-06-23 | Annexation (TIFF) (PDF) | 19-2005 | MAPPABLE | Bradley Place Subdivision: south of East Broadway (5.776 acres) |
| 2007-01-04 | Certifications of Oath of Office (TIFF) (PDF) | | | Mayor & City Commissioners |
| 2003-12-13 | Governor's Appointment (TIFF) (PDF) | Executive Order #2003-029 | | County Judge/Executive |
| 2003-12-12 | Annexation (TIFF) (PDF) | 8-2003 | MAPPABLE | Industrial Develop. Authority: n of Revilo Rd & w of L & N RR (Parcel A: 301.38a & Parcel C: 0.58a) |
| 2003-08-25 | Annexation (TIFF) (PDF) | 14-2003 | MAPPABLE | Fairholme Estates Unit 1-A: south of Fair Ave & west of Two Mile Rd (27.167 acres) |
| 2003-03-28 | Repeal of Annexation Ordinance (TIFF) (PDF) | 2-2003 | MAPPABLE | Repeals Ord 21-2002 annexing 2500 Colby Road due to procedural error. |
| 2003-03-28 | Annexation (TIFF) (PDF) | 3-2003 | MAPPABLE | First Church of God Tract: 2500 Colby Road (43.03 acres) |
| 2003-01-15 | Certification (TIFF) (PDF) | Administration of Oath | | Mayor & (4) City Commissioners |
| 2000-09-11 | Annexation (TIFF) (PDF) | 15-2000 | MAPPABLE | J & P Investments of Winchester LLC Tract: north side of Winn Avenue, Ky 15 (4.40 acres) |
| 1999-09-27 | Annexation (TIFF) (PDF) | 19-99 | MAPPABLE | Winchester Commercial LLC Tract: Lexington Avenue (11.589 acres) |
| 1999-08-30 | Annexation (TIFF) (PDF) | 16-99 | MAPPABLE | Wiseman & Littrell Tract: near intersection of bypass & Colby Rd (96.132 acres) |
| 1999-07-14 | Annexation (TIFF) (PDF) | 11-99 | MAPPABLE | Denham Tract: north side of McClure Rd between Mallard Place & Earlymeade Subdivision (1.71a) |
| 1998-04-30 | Annexation (TIFF) (PDF) | 6-98 | MAPPABLE | Earlymeade Tract with exclusions: sw of McClure Rd & Colby Rd intersection (132.53 acres) |
| 1997-11-13 | Annexation (TIFF) (PDF) | 36-97 | MAPPABLE | Multiple owners including Clark Regional Medical Center: near bypass & Colby Rd (150a) |
| 1997-06-12 | Annexation (TIFF) (PDF) | 20-97 | MAPPABLE | Multiple owners: near I-64 interchange with Winchester-Paris Rd (Clem tract excluded) |
| 1997-02-07 | Annexation (TIFF) (PDF) | 7-97 | MAPPABLE | Multiple owners including Walmart: west side of bypass & north side of Colby Rd (196.66a) |
| 1996-12-10 | Annexation (TIFF) (PDF) | 27-96 | MAPPABLE | Pinnacle Development Group Tract: 3 parcels & ROW, east side of US 627 (366 acres) |
| 1996-04-15 | Annexation (TIFF) (PDF) | 11-96 | MAPPABLE | Nelson Steel Corp. Tract: west side of Old Paris Road (8.48 acres) |
| 1996-04-15 | Annexation (TIFF) (PDF) | 12-96 | MAPPABLE | Kroger Center: west side of bypass (17.52 acres) |
| 1995-04-27 | Annexation (TIFF) (PDF) | 7-95 | MAPPABLE | Ordinance omitted. Roberts Tract: 323 Skylark Drive (0.42 acres) |
| 1993-10-08 | Annexation (TIFF) (PDF) | 24-93 | MAPPABLE | Ordinance omitted. Multiple owners including Calvary Christian Church: inside bypass (35.79 acres) |
| 1991-11-15 | Annexation (TIFF) (PDF) | 19-91 | MAPPABLE | Ordinance omitted. Adjoins Industrial Development Authority betw L & N RR & Ky 627 (242.50 acres) |
| 1991-01-04 | Annexation (TIFF) (PDF) | 39-90 | MAPPABLE | Apollo Oil, Taylor Estate & L J Investment Tract: between US 60 & I-64 nr Early Drive (83.471 acres) |
| 1985-02-28 | Annexation (TIFF) (PDF) | 1-85 | MAPPABLE | Multiple owners: north side of West Lexington Avenue (72.52 acres) |
| 1985-02-28 | Annexation (TIFF) (PDF) | 2-85 | MAPPABLE | Multiple owners: south of I-64 nr Forest Park Addition (80 acres) |
| 1981-05-07 | KRS 81.045 Filing (TIFF) (PDF) | | MAPPABLE | KRS 81.045 Filing |