| April 2002 | Hail | Monticello | 1 hurt, $500 | Windows were busted from large hail. |
| May 2025 | Thunderstorm Wind | Monticello | $55,000 | A tree was blown down onto a mobile home, also causing electrical lines to fall on the home, in the 500 block of South Main Street in Monticello. |
| January 2008 | Thunderstorm Wind | Monticello | $50,000 | Trees were blown down across roads throughout the county by winds estimated at 63 mph. |
| April 2007 | Thunderstorm Wind | Monticello | $35,000 | Numerous trees down county wide. |
| June 2009 | Thunderstorm Wind | Monticello | $30,000 | Trees and power lines down in Monticello and throughout the county. |
| July 2008 | Thunderstorm Wind | Monticello | $30,000 | Numerous trees and large limbs were blown down, especially near Lake Cumberland. |
| April 2007 | Thunderstorm Wind | Monticello | $25,000 | Numerous trees down countywide. |
| May 2025 | Hail | Monticello | $20,000 | Pictures on social media show structural damage along Cherry Street in Monticello from the large hail that fell. Multiple broken windsow and tattered vinyl siding is visible, alongside piles of large, melting hail stones. |
| March 1997 | Flash Flood | Monticello | $20,000 | no account filed |
| May 2011 | Thunderstorm Wind | Monticello | $15,000 | Trees and limbs were blown down in Monticello. |
| July 2004 | Thunderstorm Wind | Monticello | $15,000 | A barn was blown onto Route 200 in Monticello. Trees were down across the county. |
| July 2004 | Thunderstorm Wind | Monticello | $10,000 | Trees and power lines were down in the Monticello area and also northern Wayne County. |
| March 2002 | Flash Flood | Monticello | $10,000 | Heavy rains during March 17th caused repeated episodes of flash flooding. Several roads were flooded. |
| January 1997 | Thunderstorm Wind | Monticello | $10,000 | no account filed |
| May 2011 | Thunderstorm Wind | Monticello | $8,000 | Trees were blown down onto a trailer home on Evelyn Ave in Monticello. |
| August 2010 | Thunderstorm Wind | Monticello | $7,000 | Several trees were blown down in and near Monticello, blocking roads. |
| June 2021 | Thunderstorm Wind | Monticello | $6,500 | Wayne County dispatch reported that very strong thunderstorm wind gusts had caused a tree to fall onto a mobile home and vehicle along Tennessee Street just southeast of Monticello. |
| July 2017 | Thunderstorm Wind | Monticello | $5,000 | A citizen reported a couple of large tree limbs being snapped, and subsequently falling onto a nearby storage building, causing it to collapse. |
| September 2010 | Thunderstorm Wind | Monticello | $5,000 | Multiple trees were blown down outside the Wayne County Hospital. |
| June 2009 | Thunderstorm Wind | Monticello | $5,000 | Trees were blown down in the city of Monticello at the intersection of College and Alexander Streets. |
| June 2006 | Thunderstorm Wind | Monticello | $5,000 | Numerous trees down over south portion of the county. Power out in Monticello for a couple of hours. |
| August 2005 | Thunderstorm Wind | Monticello | $5,000 | Trees down across an area around 200 yards wide along Highway 92 East near Monticello. One tree fell on a house and a roof was blown off a garage. |
| May 2011 | Thunderstorm Wind | Monticello | $4,000 | A few trees and large limbs were reported to have been blown down in Monticello. |
| July 2012 | Thunderstorm Wind | Monticello | $3,000 | Trees were blown down and the siding was blown off of a garage on Missouri Hollow Rd. |
| January 1999 | Thunderstorm Wind | Monticello | $3,000 | Trailer roof blown off. |
| March 2020 | Thunderstorm Wind | Monticello | $2,000 | Dispatch reported a tree blown down just southwest of Monticello as a strong thunderstorm moved overhead. |
| April 2011 | Thunderstorm Wind | Monticello | $2,000 | There were trees down on Hollow road. |
| April 2011 | Thunderstorm Wind | Monticello | $2,000 | There were trees down on highway 200 at Flat Springs. |
| May 2009 | Thunderstorm Wind | Monticello | $2,000 | A couple of trees were blown down in the Monticello area; one on Hwy 5 west on KY Hwy 200 and the other 2 miles northeast on KY Hwy 3285. High water was over roads county wide but no roads were closed. |
| April 2006 | Thunderstorm Wind | Monticello | $2,000 | Power lines blown down. |
| April 2006 | Thunderstorm Wind | Monticello | $2,000 | Several trees down on powerlines. |
| June 2006 | Thunderstorm Wind | Monticello | $2,000 | Tree down and broke power line at Rogers Grove. |
| August 2013 | Flash Flood | Monticello | $1,000 | Highway 92 was closed near Hwy776. Highway 167 was also closed a few miles out of town. |
| June 2011 | Thunderstorm Wind | Monticello | $1,000 | A tree was blown down and across Hwy 200 in the Number One community. |
| May 2010 | Hail | Monticello | $1,000 | One inch hail and a downed tree were reported at Betsey. |
| August 2010 | Thunderstorm Wind | Monticello | $1,000 | A tree was blown down on KY Hwy 858. |
| January 2008 | Thunderstorm Wind | Monticello | $1,000 | One tree was blown down near the intersection of Highways 200 and 834 by wind gusts estimated at 61 mph. |
| July 2005 | Thunderstorm Wind | Monticello | $1,000 | Large tree limbs down on power lines on Old Missouri Hollow Road. |
| May 2025 | Thunderstorm Wind | Monticello | - | A tree was blown down and was blocking Michigan Avenue in Monticello, adjacent to the Monticello Wayne County Park. |
| April 2025 | Thunderstorm Wind | Monticello | - | Wayne County 911 reports trees downed on Dugan Street in Monticello. |
| May 2025 | Hail | Monticello | - | A picture on social media showed piles of melting large hail along Michigan Avenue in Monticello. Some of these stones are at least quarter-sized even after melting some, and the ground is completely covered. Vehicles are also covered in tree debris from the falling hail. |
| May 2025 | Hail | Monticello | - | Large amounts of ping pong ball sized hail was reported near the Doughboy Statue on Main Street in downtown Monticello. |
| May 2025 | Hail | Monticello | - | Multiple reports of broken windows and damaged vinyl siding were made in Monticello for the large hail this evening. At a residence along Bob Carrender Road (Donnie Patton Rd), there were photos of holes in the siding, with hail estimated to be at least ping pong ball sized. |
| May 2024 | Flash Flood | Monticello | - | North Main Street was closed in front of the Monticello City Fire Department due to flooding. |
| May 2024 | Hail | Monticello | - | A public report of quarter sized hail was made in Monticello. |
| June 2022 | Thunderstorm Wind | Monticello | - | A tree was blown down and across KY-167 in the 700 block near Monticello. |
| June 2022 | Thunderstorm Wind | Monticello | - | Two large trees were blown down on KY-1275 N in the 600 block near Monticello. |
| February 2019 | Flood | Monticello | - | Law enforcement reported flooding throughout Monticello. This includes along Kentucky Highways 3284, 92, and 167. |
| June 2019 | Thunderstorm Wind | Monticello | - | Local media reported a few trees down throughout Monticello due to the saturated ground. These were found on Ridgewood Avenue, Hickory Hill Drive, and Columbia Avenue. |
| May 2017 | Hail | Monticello | - | A trained spotter observed nickel sized hail in Monticello. |
| May 2016 | Thunderstorm Wind | Monticello | - | Dispatch relayed reports of several trees blown down on Missouri Hollow Road and Morris Hill Road as a line of thunderstorms moved south of Monticello. |
| June 2015 | Thunderstorm Wind | Monticello | - | Trees were blown down. |
| May 2013 | Thunderstorm Wind | Monticello | - | Trees were blown down in Monticello. |
| June 2013 | Thunderstorm Wind | Monticello | - | Tree limbs were blown down onto power lines, leading to power outages in the area. Pea size hail was also reported. |
| June 2013 | Thunderstorm Wind | Monticello | - | Trees and power lines were blown down in Monticello. |
| July 2012 | Thunderstorm Wind | Monticello | - | Several trees were blown down in Monticello. |
| March 2012 | Thunderstorm Wind | Monticello | - | A thunderstorm wind gust of 58 mph occurred 2 miles north of Monticello. |
| September 2012 | Heavy Rain | Monticello | - | According to a cooperative weather observer, 2.83 inches of rain fell in Monticello. |
| January 2010 | Heavy Rain | Monticello | - | As a result of heavy rainfall, four inches of water was reported running over Highway 92 in Monticello. |
| May 2010 | Hail | Monticello | - | Quarter size hail fell at Murl. |
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