| July 1999 | Lightning | Chipley | $75,000 | Lightning sparked a fire which destroyed a residence on Brickyard Rd. |
| November 1995 | Tornado (F1) | Chipley | $20,000 | A tornado damaged a dairy. |
| July 1997 | Flash Flood | Chipley | $20,000 | no account filed |
| July 1995 | Thunderstorm Wind | Chipley | $15,000 | Washington County Emergency Management reported several downed trees and power outages. A mobile home was cut in half by a falling tree. |
| April 2011 | Thunderstorm Wind | Chipley | $10,000 | Trees were blown down in Chipley and across the county. The monetary damage figure provided is a rough estimate. |
| September 2011 | Thunderstorm Wind | Chipley | $5,000 | Trees were blown down county wide. The monetary damage figure provided is a rough estimate. |
| March 2005 | Thunderstorm Wind | Chipley | $5,000 | The public reported numerous downed trees and power lines in the Sunnyhills subdivision. |
| December 2000 | Thunderstorm Wind | Chipley | $5,000 | Trees and power lines down just west of Highway 77. Reported by the Washington County EMA. |
| June 1994 | Tornado (F0) | Chipley | $5,000 | A roof was blown off of a house and numerous trees, and power lines were blown down in Orange Hill area. |
| January 2013 | Thunderstorm Wind | Chipley | $4,000 | Multiple trees and power lines were blown down near Chipley. Monetary damage was estimated. |
| June 2018 | Thunderstorm Wind | Chipley | $3,000 | Trees and power lines were blown down in Chipley. |
| August 2016 | Flash Flood | Chipley | $3,000 | Several streets were flooded and closed during a period of heavy rainfall, including South Blvd, 4th Street, 5th Street, and North Railroad Ave. There was minor structural flooding as well in Chipley. The water receded about an hour after the rain ended. |
| April 2015 | Thunderstorm Wind | Chipley | $3,000 | Trees and power lines were blown down in the northern part of Washington county. |
| June 2008 | Thunderstorm Wind | Chipley | $3,000 | Several trees and power lines were down across State Highway 77. |
| June 2025 | Thunderstorm Wind | Chipley | $2,000 | Trees and power lines were blown down in and around Chipley. |
| March 2021 | Thunderstorm Wind | Chipley | $2,000 | A few trees were blown down in the Chipley area, including one on a power line. |
| August 2020 | Thunderstorm Wind | Chipley | $2,000 | A tree was blown down along with multiple power lines. |
| February 2016 | Thunderstorm Wind | Chipley | $2,000 | A tree was blown down onto the corner of a carport on the north side of Chipley. This was a public post to the WMBB-TV facebook page. There were also other reports of tree damage in Chipley. |
| September 2015 | Lightning | Chipley | $2,000 | Lightning caused several power outages in Chipley. |
| September 2015 | Thunderstorm Wind | Chipley | $2,000 | A tree and a power line were blown down near Chipley. |
| September 2018 | Thunderstorm Wind | Chipley | $1,000 | A power line was blown down near North Railroad Ave and 2nd Street in Chipley. |
| December 2012 | Thunderstorm Wind | Chipley | $1,000 | A power line was blown down on Morris Street in Chipley. Monetary damage was estimated. |
| May 2006 | Thunderstorm Wind | Chipley | $1,000 | The Washington County Sheriff reported numerous trees down across Gainer Road in Chipley. |
| January 2026 | Thunderstorm Wind | Chipley | - | A tree was blown down onto Church Ave near Coopers. |
| February 2025 | Thunderstorm Wind | Chipley | - | A tree was blown down onto Brown Dr at Wynn Dr in Chipley. |
| May 2024 | Flash Flood | Chipley | - | Fifth Street and Old Bonifay Road was flooded. |
| September 2024 | Flash Flood | Chipley | - | Water was reported over roadways along South Blvd from 2nd Street to Highway 77. |
| September 2024 | Flash Flood | Chipley | - | Water was reported over roadways near Brickyard Road and Orange Hill Road. |
| May 2023 | Flood | Chipley | - | Minor flooding was reported along Old Bonifay Road at 5th Street in Chipley. |
| May 2023 | Flood | Chipley | - | Minor flooding was reported along Old Bonifay Road and Griffin Road. |
| March 2022 | Flash Flood | Chipley | - | Roads were flooded in Chipley. |
| June 2022 | Thunderstorm Wind | Chipley | - | A tree was blown down on Highway 273 with two power lines also down. |
| June 2022 | Thunderstorm Wind | Chipley | - | Around 16 trees were blown down across the county. |
| July 2020 | Thunderstorm Wind | Chipley | - | Multiple trees were blown down in Chipley. |
| September 2020 | Flash Flood | Chipley | - | Highway 90 west of Hoyt St was reported underwater. |
| April 2020 | Thunderstorm Wind | Chipley | - | Trees were blown down in the Chipley area. |
| July 2019 | Thunderstorm Wind | Chipley | - | A tree was blown down onto Highway 77 in Chipley. |
| April 2017 | Thunderstorm Wind | Chipley | - | Three power lines were blown down in Chipley. |
| August 2016 | Flash Flood | Chipley | - | The Florida Highway Patrol reported that Griffin Road at U.S. Highway 90 was closed due to flooding. |
| April 2015 | Flash Flood | Chipley | - | Some roads were blocked off due to flooding around Old Bonifay Road and Martin Luther King Road, mainly north of Highway 90. |
| April 2014 | Flash Flood | Chipley | - | Highway 90 and Sinclair was flooded due to heavy rain in a short period of time. |
| April 2014 | Flash Flood | Chipley | - | The intersections of Old Bonifay Road and Main Street as well as Old Bonifay Road and 5th Street were flooded in Chipley. |
| June 2012 | Thunderstorm Wind | Chipley | - | Large tree limbs were blown down. The largest was about a foot in diameter and 20 feet long. |
| February 2012 | Heavy Rain | Chipley | - | A 24 hour rainfall total of 5.00 inches was reported by a COOP Observer near Chipley. |
| February 2012 | Flash Flood | Chipley | - | The Washington county 911 call center reported that 4 roads were closed around the Chipley area due to flash flooding. Very heavy rainfall rates up to 4 inches per hour were reported in nearby in neighboring Holmes county, and widespread rainfall amounts of 3 to 5 inches occurred in just a few hours. |
| May 2010 | Heavy Rain | Chipley | - | A storm total rainfall of 6.52 inches was reported. |
| February 2008 | Hail | Chipley | - | Penny size hail was reported in Chipley. |
| July 2007 | Thunderstorm Wind | Chipley | - | A few trees were down on Rowland Road and Haley Drive. |
| August 2007 | Hail | Chipley | - | Penny size hail was reported. |
| September 2007 | Funnel Cloud | Chipley | - | A funnel cloud was sighted just north of Interstate 10. |
| March 2005 | Hail | Chipley | - | Golfball size hail reported in the Sunnyhills subdivision by WJHG-TV in Panama City. |
| November 1997 | Hail | Chipley | - | Washington County Sheriff observed nickel size hail in Chipley. |
| March 1996 | Thunderstorm Wind | Chipley | - | no account filed |