| May 2004 | Tornado (F1) | Winchester | 1 killed, 1 hurt | The tornado initially touched down 6 miles west southwest of Winchester then traveled to the northeast causing minor tree damage. Two miles southwest of Winchester it destroyed a mobile home causing 1 fatality. The two occupants of the mobile home were thrown from the home. The husband only sustained minor injuries. As the tornado went through Winchester it weakened in intensity causing minor to moderate damage to the roofs of several homes, destroyed some sheds and blew down numerous trees. |
| June 2011 | Thunderstorm Wind | Winchester | $200,000 | Several trees and tree limbs were blown down in Winchester. In addition, 15 large power poles were snapped, resulting in a widespread power outage. |
| July 2015 | Thunderstorm Wind | Winchester | $40,000 | Numerous trees and power lines were blown down about 3 miles southwest of Winchester. |
| September 2008 | Flash Flood | Winchester | $25,000 | Route 106 south of Winchester was closed due to high water. In addition, there were numerous reports of flooded basements in Winchester. |
| July 2014 | Thunderstorm Wind | Winchester | $18,000 | Several tree limbs were blown down. |
| February 2011 | Thunderstorm Wind | Winchester | $15,000 | A roof was blown off a utility shed and a 10-inch diameter tree was knocked down. |
| June 2010 | Thunderstorm Wind | Winchester | $12,000 | Several tree limbs and one power line were blown down. |
| July 2008 | Thunderstorm Wind | Winchester | $2,000 | A large tree was blown down on the west side of Winchester. |
| September 2014 | Thunderstorm Wind | Winchester | $1,500 | A large tree was blown across the Winchester/Glasgow Blacktop. |
| June 2011 | Thunderstorm Wind | Winchester | $1,000 | A large tree limb was blown down onto Commercial Street in Winchester. |
| May 1998 | Thunderstorm Wind | Winchester | $1,000 | As a severe thunderstorm moved southeast across Scott County it blew down numerous trees and power lines in Winchester, Glasgow, Alsey, and Manchester. No injuries were reported. |
| June 1995 | Thunderstorm Wind | Winchester | $100 | A local newspaper reported tree limbs about six inches in diameter snapped off from high wind gusts. |
| June 2025 | Thunderstorm Wind | Winchester | - | Numerous small tree limbs between one and six inches in diameter were broken, and an area of corn was flattened. |
| May 2024 | Thunderstorm Wind | Winchester | - | A tree was blown down resulting in a power outage. |
| May 2024 | Flash Flood | Winchester | - | Cherry Street and Cross Street were closed due to flooding. |
| August 2024 | Thunderstorm Wind | Winchester | - | A few trees and tree branches were blown down. |
| June 2023 | Thunderstorm Wind | Winchester | - | A large tree was blown down and destroyed a trampoline. |
| June 2022 | Thunderstorm Wind | Winchester | - | Numerous trees were blown down in Winchester, some of which were broken in half. |
| May 2011 | Thunderstorm Wind | Winchester | - | Several trees, tree branches, and power lines were blown down in Winchester. |
| May 2010 | Flash Flood | Winchester | - | Slow moving thunderstorms produced 3.00 to 4.00 inches of rain in 2 hours across southern Scott County. Many rural roads were impassable, including Illinois Route 106 from Alsey to the Greene County line. |
| June 2008 | Flash Flood | Winchester | - | High water was flowing over roads in numerous locations between Winchester and Jacksonville. |
| August 2007 | Thunderstorm Wind | Winchester | - | A cornfield was flattened and several tree limbs were blown down.| |
| July 2006 | Thunderstorm Wind | Winchester | - | Several trees were blown down. |
| October 2004 | Thunderstorm Wind | Winchester | - | A large tree was blown down on a power line. |
| July 2003 | Thunderstorm Wind | Winchester | - | Several trees and tree limbs were blown down. |
| May 2003 | Flash Flood | Winchester | - | Very heavy rain fell over Scott county, causing several roads to be flooded. Illinois Route 106 in Winchester was briefly flooded. |
| August 2003 | Thunderstorm Wind | Winchester | - | Several large tree limbs were blown down near Illinois Route 106. |
| June 2002 | Thunderstorm Wind | Winchester | - | Thunderstorm winds blew down several power lines in town. |
| July 2002 | Thunderstorm Wind | Winchester | - | A tree was blown over. |
| August 2001 | Thunderstorm Wind | Winchester | - | Several trees and power lines were blown down. |
| July 2001 | Thunderstorm Wind | Winchester | - | Several power lines were blown down in Winchester, Alsey and Glasgow. |
| May 2000 | Thunderstorm Wind | Winchester | - | A two to two and a half mile wide swath of damage extended from 3.8 miles west of Winchester to 1 and a quarter miles north of Winchester to 5 miles northeast of Winchester then into Morgan County. Most of the damage was to trees, power lines, and power poles. |
| May 2000 | Tornado (F0) | Winchester | - | A tornado which formed along the leading edge of a bow echo touched down in Pike County (WFO St. Louis CWA) 2.5 miles southeast of Detroit, then traveled to the east northeast, crossing the Illinois River south of Florence. It moved into Scott County (WFO Central Illinois CWA) 8 miles west southwest of Winchester, but little damage was found in the river bottoms area until the tornado moved up into the bluffs. About four miles west of Winchester, it flattened corn, uprooted several trees, snapped a couple of utility poles, damaged an outbuilding, and caused minor damage to two homes before lifting and dissipating. No injuries were reported. |
| July 2000 | Thunderstorm Wind | Winchester | - | Several trees were blown down in Winchester. One tree fell onto IL Route 106 east of town and another one fell onto Main street in downtown Winchester, briefly blocking it. No injuries were reported. |
| November 1998 | Thunderstorm Wind | Winchester | - | Numerous large tree limbs were blown down. |
| August 1993 | Thunderstorm Wind | Winchester | - | Winds estimated at 60 mph knocked several large ceramic flower pots over. |
| March 2024 | Hail | Winchester | - | no account filed |
| August 2024 | Hail | Winchester | - | no account filed |
| July 2023 | Hail | Winchester | - | no account filed |
| March 2016 | Hail | Winchester | - | no account filed |
| June 2011 | Hail | Winchester | - | no account filed |
| May 2011 | Hail | Winchester | - | no account filed |
| May 2011 | Hail | Winchester | - | no account filed |
| May 2009 | Hail | Winchester | - | no account filed |
| August 2009 | Hail | Winchester | - | no account filed |
| August 2009 | Hail | Winchester | - | no account filed |
| March 2006 | Hail | Winchester | - | no account filed |
| May 2004 | Hail | Winchester | - | no account filed |
| May 2003 | Hail | Winchester | - | no account filed |
| May 2002 | Flash Flood | Winchester | - | no account filed |
| June 2001 | Hail | Winchester | - | no account filed |
| June 1998 | Hail | Winchester | - | no account filed |
| May 1998 | Hail | Winchester | - | no account filed |
| April 1996 | Tornado (F0) | Winchester | - | no account filed |
| April 1996 | Thunderstorm Wind | Winchester | - | no account filed |