| April 2007 | Thunderstorm Wind | Middlesboro | $100,000 | Numerous trees and powerlines down throughout the county. Roof and siding damage to a few homes in the Dorton Branch area. |
| July 2012 | Thunderstorm Wind | Middlesboro | $50,000 | The roof of a Big Lots store and various other business signs along Hwy 25E were damaged or blown away completely. |
| June 1998 | Lightning | Middlesboro | $50,000 | Lightning struck and burned up a transformer. |
| November 1996 | Flash Flood | Middlesboro | $20,000 | no account filed |
| March 2012 | Thunderstorm Wind | Middlesboro | $15,000 | Trees were blown down in Middlesboro. |
| March 1997 | Flash Flood | Middlesboro | $10,000 | no account filed |
| February 2011 | Thunderstorm Wind | Middlesboro | $8,000 | An 8 by 12 foot shed was moved about 40 feet by a thunderstorm wind gust. A few shingles and some siding was torn off one structure. An unsupported concrete block wall was also knocked over. The damage occurred at the corner of 23rd and Winchester Streets in Middlesboro. |
| February 2008 | Thunderstorm Wind | Middlesboro | $8,000 | Both trees and powerlines were blown down along Highway 2079. |
| April 2011 | Thunderstorm Wind | Middlesboro | $6,000 | Trees were blown down and onto power lines at the Bella Gardens Apt complex on Old Pineville Pike in Middlesboro. |
| April 2011 | Thunderstorm Wind | Middlesboro | $5,000 | There were trees blown down on the right fork of Polly Hollow Rd outside of Middlesboro. |
| June 2006 | Thunderstorm Wind | Middlesboro | $5,000 | One tree down in Spade Acres in Middlesboro. Trees down on Highway 987 towards Cubage. Power outages in the Ferndale area south of Pineville. |
| June 2011 | Thunderstorm Wind | Middlesboro | $3,000 | A tree and large tree limbs were blown down by thunderstorm wind gusts in Middlesboro. |
| June 1998 | Thunderstorm Wind | Middlesboro | $3,000 | Trees and power lines downed. |
| June 1997 | Tornado (F0) | Middlesboro | $3,000 | A small tornado damaged trees and downed power lines. |
| May 2010 | Thunderstorm Wind | Middlesboro | $2,000 | Two good sized trees were blown down in city limits. There was also ankle deep water on most streets and parking lots. |
| November 2007 | Thunderstorm Wind | Middlesboro | $2,000 | Two trees were blown down in Cumberland Gap NHP. Time was estimated from radar. |
| July 1999 | Thunderstorm Wind | Middlesboro | $2,000 | Strong winds blew several trees down onto power lines across the town of Middlesboro. Approximately one-third of the town was without power for several hours. |
| May 2024 | Thunderstorm Wind | Middlesboro | $1,000 | Tree was reported down onto power lines on Edgewood Road in Middlesboro via a social media report. |
| May 2025 | Hail | Middlesboro | - | A public report on social media of quarter sized hail in Middlesboro. |
| May 2024 | Thunderstorm Wind | Middlesboro | - | A social media report with drone photos showed large trees down on the east side of Middlesboro. |
| May 2024 | Thunderstorm Wind | Middlesboro | - | Many trees were blown down around the city of Middlesboro. |
| September 2023 | Heavy Rain | Middlesboro | - | The National Park Service YELK2 RAWS site at Cumberland Gap recorded 1.68 inches of rainfall in 1 hour. |
| September 2023 | Flash Flood | Middlesboro | - | Middlesboro Police Department reported that Cumberland Avenue was closed between 15th and 19th Streets due to flash flooding. |
| September 2023 | Flash Flood | Middlesboro | - | Middlesboro Police Department reported that North 15th Street was closed at Ashbury Avenue in the vicinity of Little Yellow Creek due to flash flooding. |
| September 2023 | Heavy Rain | Middlesboro | - | A two hour rainfall total of 4 inches was recorded at the Cumberland Gap National Park Service RAWS - YELK2. |
| July 2022 | Thunderstorm Wind | Middlesboro | - | Pictures on social media show a large portion of a pine tree sanpped off in someone's yard along West Chester Avenue in Middlesboro. |
| March 2021 | Heavy Rain | Middlesboro | - | The YELK2 (Yellow Creek) RAWS observing site near Cumberland Gap measured 4.34 inches of rainfall in a 24 hour period. |
| June 2015 | Thunderstorm Wind | Middlesboro | - | A tree was blown down. |
| April 2014 | Thunderstorm Wind | Middlesboro | - | One tree was reported to have been blown down. This report was a public report relayed via social media. |
| June 2014 | Thunderstorm Wind | Middlesboro | - | One tree was downed by thunderstorm winds. |
| January 2013 | Thunderstorm Wind | Middlesboro | - | Tree was reported down on Hwy 74. |
| February 2011 | Heavy Rain | Middlesboro | - | Two inches of rain fell along Clear Creek in Middlesboro. |
| June 2011 | Heavy Rain | Middlesboro | - | A rainfall total of 4.42 inches was measured by the Middlesboro Bell county Airport AWOS between 235 and 635 am, with 1.88 inches of that rain falling between 535 and 635 am. |
| June 2011 | Heavy Rain | Middlesboro | - | It was reported that 5.71 inches of rain had fallen near Middlesboro between 3 and 725 am, with 1.26 inches of that total accumulating between 625 and 725 am. |
| June 2011 | Heavy Rain | Middlesboro | - | The Yellow Creek RAWS site measured a three hour rainfall total of 3.05 inches. |
| June 2011 | Flash Flood | Middlesboro | - | Numerous roads were under water throughout Middlesboro, including 35th, 19th, and 25A. A spotter reported that at least 3-4 inches of rain had fallen overnight. |
| May 2006 | Thunderstorm Wind | Middlesboro | - | Few trees down at 25th Street, Cumberland Ave, and Fords Woods Park. |
| August 2006 | Thunderstorm Wind | Middlesboro | - | Tree down behind West End School. Tree down and blocking Airport Road. Trees also down at various locations across the county. |
| March 2005 | Flash Flood | Middlesboro | - | An area of showers and thunderstorms formed ahead of an eastward moving cold front, leading to flash flooding of creeks and streams in the Middlesboro area. |
| July 2005 | Thunderstorm Wind | Middlesboro | - | Trees down on Exeter and Chester Avenues. |
| July 2004 | Thunderstorm Wind | Middlesboro | - | Several trees were down on 24th Street. |
| April 2002 | Thunderstorm Wind | Middlesboro | - | Trees and large branches were down. |
| November 2002 | Hail | Middlesboro | - | Three quarter inch diameter hail was reported along United States Highway 25 East. |
| April 2000 | Flash Flood | Middlesboro | - | Heavy rains produced flooding in Middlesboro. Several roads had to be closed due to the high water. |
| March 2012 | Hail | Middlesboro | - | no account filed |
| March 2012 | Hail | Middlesboro | - | no account filed |
| March 2012 | Hail | Middlesboro | - | no account filed |
| May 2010 | Hail | Middlesboro | - | no account filed |
| June 2009 | Funnel Cloud | Middlesboro | - | no account filed |
| July 2008 | Hail | Middlesboro | - | no account filed |
| April 2006 | Hail | Middlesboro | - | no account filed |
| November 2002 | Hail | Middlesboro | - | no account filed |
| November 2002 | Hail | Middlesboro | - | no account filed |
| April 1998 | Hail | Middlesboro | - | no account filed |
| January 1997 | Thunderstorm Wind | Middlesboro | - | no account filed |
| January 1997 | Thunderstorm Wind | Middlesboro | - | no account filed |