| April 1974 | Tornado (F3) | not stated | 1 killed, 7 hurt, $2,500,000 | no account filed |
| June 1999 | Lightning | Plymouth | 2 hurt | no account filed |
| August 1966 | Tornado (F1) | not stated | 1 hurt, $250,000 | no account filed |
| August 2015 | Thunderstorm Wind | Haven | 1 hurt, $1,000 | A flag pole fell on an individual, who suffered a broken arm, at the Whistling Straits golf course during the PGA Championship. The leaderboard was also blown over. |
| August 1998 | Flash Flood | Sheboygan | $40,000,000 | no account filed |
| August 2018 | Thunderstorm Wind | Parnell | $1,400,000 | A swath of widespread tree and crop damage across the southern portion of the county. Sections of trees and crops completely flattened, and some structural damage from fallen trees or due to the strong downburst winds. Various roads closed due to fallen trees. Two semi-trucks were overturned on highway 57 in Waldo. The widespread wind damage and tornadoes caused structural damage to many homes with 70 homes sustaining affected damage, 3 homes with minor damage, 2 homes with major damage, one home destroyed, and 2 businesses with minor damage. |
| May 1998 | Thunderstorm Wind | Countywide | $642,000 | no account filed |
| June 2008 | Flash Flood | Waldo | $402,300 | Heavy rains resulted in flash flooding across parts of eastern Sheboygan County. Water depths on road surfaces reached 3 feet or more and there were gravel washouts. Erosion damage was noted at Kohler Andrae State Park. Some farm fields remained flooded into early July. The breakdown for residential home losses were: 30 minimally affected, and 30 with minor damage (total of $148.5 thousand for home losses). There were no business losses. Crop losses were estimated at $300 thousand. Public sector damage was about $253.9 thousand. A couple roads and bridges sustained minor damage. |
| April 2006 | Thunderstorm Wind | Elkhart Lake | $400,000 | no account filed |
| April 2001 | Thunderstorm Wind | Greenbush | $400,000 | no account filed |
| July 2008 | Tornado (EF1) | (Sbm)Sheboygan Co Ar | $350,000 | This tornado spun up on the front side of a line of thunderstorms in association with a strong microburst that rotated around on itself. It damaged an airport hangar door, destroyed 3 barns, damaged 2 other barns, lightly damaged 3 homes, took the top 1/3 of a silo down, damaged 2 other silos, and uprooted or snapped many trees. Only some minor corn crop damage was noted. It was observed by several people. This tornado started on the east side of the Sheboygan County Airport, and moved east-southeast and eventually crossed STH 32 about midway between STH 23 and CTH O. Once it crossed STH 32 it curved sharply to a south-southeast bearing and dissipated northeast of the intersection of STH 23 and STH 32. It's starting and ending pairs of lat/long numbers were: 43.76517/-87.84273 and 43.75375/-87.81711. DI#1 (SBO), DOD6. The winds were estimated at about 95 mph. The average path width was about 30 yards. |
| July 2008 | Thunderstorm Wind | Greenbush | $300,000 | A line of severe storms moved west to east across Sheboygan County and generated widespread powerful winds that gusted to an estimated 61 to 70 knots (70 to 80 mph). In addition, a tornado spun up north of Sheboygan Falls at 1437 CST - see the tornado event write-up for deatils. The ASOS unit at the Sheboygan County Airport measured a gust of 53 knots (61 mph). Thousands of trees were snapped or toppled, and many power-lines were brought down by tree debris, mostly across the northern part of the county. An 81-year-old women in Plymouth was injured when the winds pushed a door of a store into her. She broke her arm and was hospitalized. Elsewhere in Plymouth, 2 vehicles were damaged by tree debris. North of Plymouth, 2 cabins at a camp ground were destroyed by toppled trees, and 3 other camp buldings were damaged. In Sheboygan Falls, at least 12 homes were damaged. In Kohler, a vehicle was crushed by a toppled tree. City and county 911 Communications Centers received thousands of calls within a 5 hour period. At least 14,000 homes in Sheboygan County lost electrical power. |
| July 1996 | Tornado (F1) | Beechwood | $250,000 | no account filed |
| July 1987 | Tornado (F1) | not stated | $250,000 | no account filed |
| June 2008 | Flash Flood | Plymouth | $150,000 | Heavy rains resulted in flash flooding around Plymouth and south to the county line. Water depths on road surfaces reached 3 feet or more and there were gravel washouts. Some farm fields remained flooded into early July. The breakdown for residential home losses were: 20 minimally affected, and 20 with minor damage (total of $50 thousand for home losses). There were no business losses. Crop losses were estimated at $200 thousand. Public sector damage was about $100 thousand. A couple roads and bridges sustained damage. |
| June 1997 | Flash Flood | Oostburg | $150,000 | no account filed |
| May 2004 | Lightning | Random Lake | $130,000 | no account filed |
| August 1996 | Lightning | Waldo | $130,000 | no account filed |
| July 2006 | Thunderstorm Wind | Oostburg | $100,000 | Barn reported down with horses inside northeast of Oostburg. A roof antenna and weather station south of Sheboygan were damaged by the wind gusts. Tree and power-line damage around the city of Sheboygan where about 12,000 customers were without power. City work crews in Sheboygan had about 200 locations across the city where tree debris had to be cleaned up. Clean-up and overtime costs were unknown, but were probably substantial. Several homes had trees leaning onto roofs, and and least one vehicle was damaged when a tree fell on it. |
| May 2010 | Thunderstorm Wind | Elkhart Lake | $75,000 | Powerful thunderstorm winds toppled about three dozen large trees and resultant tree debris knocked down at least a dozen to two dozen power-lines. About 800 customers lost electrical power, but by 2200 CST all power was restored. One light pole was knocked down at Lincoln St. and Rhine St. in the Elkhart Lake area. One tree fell onto an automobile at the Osthoff Resort near Elkhart Lake and damaged it. |
| September 2005 | Thunderstorm Wind | Cedar Grove | $75,000 | Trees and power lines were blown down and a few houses sustained some minor damage. |
| June 2022 | Thunderstorm Wind | Erdman | $60,000 | A swath of large trees snapped or uprooted. Some trees fallen on houses and cars. Many power lines down. |
| June 2022 | Thunderstorm Wind | Waldo | $60,000 | A swath of structural damage to barns and outbuildings in the Lima area. |
| May 2020 | Flood | Haven | $50,000 | Water over roads in low-lying areas all over the county with some closures. Many people in the City of Sheboygan had water in their basements due to the storm sewer backing up. |
| July 2008 | Flash Flood | Howards Grove | $40,000 | Heavy rains of 4 inches to over 5 inches affected the Howards Grove area during the mid and late afternoon hours as a line of strong to severe thunderstorms moved east through the area. The heavy rains triggered a flash flood that generated water depths of 1 to 3 feet on some streets. In addition, the middle school flooded, and damage to its gym floor amounted to at least $30,000. Some basements flooded as well, with damage to contents. |
| July 1999 | Thunderstorm Wind | Sheboygan | $40,000 | no account filed |
| June 2020 | Thunderstorm Wind | Plymouth | $30,000 | A barn was toppled by strong winds. |
| May 2017 | Thunderstorm Wind | Waldo | $30,000 | A barn blown down and two 2X4s blown into a nearby house. |
| August 2000 | Flash Flood | Plymouth | $30,000 | no account filed |
| June 2001 | Thunderstorm Wind | Elkhart Lake | $25,000 | no account filed |
| August 2001 | Thunderstorm Wind | Elkhart Lake | $25,000 | no account filed |
| September 1999 | Lightning | Plymouth | $25,000 | no account filed |
| August 1998 | Lightning | Sheboygan | $25,000 | no account filed |
| July 1973 | Tornado (F1) | not stated | $25,000 | no account filed |
| May 2010 | Lightning | Sheboygan Co Mem Arp | $20,000 | Lightning struck and damaged an electrical overhead system on a line just south of the intersection of County Highways J and M. About 500 customers were without power for about 4 hours. |
| July 2010 | Flash Flood | Sheboygan | $20,000 | A trained spotter reported 3 feet of water over South Business Drive between Riverdale Avenue and Stahl Road in the town of Wilson 5 miles south-southwest of Sheboygan. Another trained spotter reported street flooding on the south side of the city of Sheboygan near the intersection of Weeden Creek road and 10th Street. The flooding damaged the contents of flooded basements and washed out gravel shoulders of roads. |
| July 2008 | Lightning | Cedar Grove | $20,000 | A newspaper article noted that lightning struck a cabin somewhere in the Civil Town of Holland, and the resultant fire damaged the building. Cedar Grove was used only as a nearby reference point. |
| July 2002 | Thunderstorm Wind | Beechwood | $20,000 | no account filed |
| July 1999 | Thunderstorm Wind | Greenbush | $20,000 | no account filed |
| July 1996 | Thunderstorm Wind | Plymouth | $20,000 | no account filed |
| August 2021 | Flash Flood | Elkhart Lake | $15,000 | County Road MM was reported underwater where it intersects the Sheboygan River. Nearby on MM closer to highway J, two vehicles stuck in flood waters in the ditch. |
| May 2017 | Thunderstorm Wind | Batavia | $15,000 | A grain bin was blown over. |
| March 2013 | Flood | Kohler | $15,000 | The Sheboygan near Sheboygan crested at 11.54 feet, 3.54 feet above flood stage, at 805 pm CDT on March 12th. |
| August 1996 | Thunderstorm Wind | Glenbeulah | $15,000 | no account filed |
| August 2023 | Thunderstorm Wind | Elkhart Lake | $10,000 | Numerous trees down. |
| October 2019 | Flash Flood | Haven | $10,000 | Several roads were flooded and closed across the county after several inches of rain. This included highway 144 from highway 28 to highway I west of Random Lake. Flooding of streets in Plymouth and Sheboygan with water up to 2 feet in some intersections. |
| March 2019 | Flood | Franklin | $10,000 | The Sheboygan River flooded in the Town of Herman. Several homes and businesses were flooded on Main St. and Franklin Rd. The river was flowing over the Main St. bridge. An ice jam may have been occurring but was not confirmed. |
| July 2015 | Thunderstorm Wind | Beechwood | $10,000 | Widespread tree damage with some power outages. |
| August 2015 | Thunderstorm Wind | Elkhart Lake | $10,000 | A swath of large trees downed. |
| August 2015 | Thunderstorm Wind | Edwards | $10,000 | Numerous trees down and some powerlines down. |
| July 2015 | Thunderstorm Wind | Greenbush | $10,000 | Branches and trees down in the northern portion of the county including Plymouth. |
| April 2013 | Flood | Kohler | $10,000 | The Sheboygan River in Sheboygan experienced moderate flooding, cresting at 10.23 feet, or 2.23 feet over the flood stage of 8 feet, at 925 PM CDT on April 11th. |
| August 2013 | Thunderstorm Wind | Elkhart Lake | $10,000 | A sporadic 3 mile path of trees and power lines down. |
| July 2010 | Lightning | Plymouth | $10,000 | A lightning strike to a power pole near Plymouth destroyed insulators and damaged wire conductors, knocking out power to about 500 customers. Power was off to these customers for around 45 minutes. |
| August 2008 | Thunderstorm Wind | Elkhart Lake | $10,000 | Powerful downburst straight-line winds toppled many large trees. Tree debris knocked down some power-lines. |
| April 2008 | Flash Flood | Waldo | $10,000 | Heavy rains due to training thunderstorms resulted in brief flash flooding in on the northwest side of Waldo. There were gravel shoulder washouts and mud deposits on roads near a creek that feeds into Waldo Mill Pond. Water depths on roads were at least 6 inches. |
| July 2006 | Thunderstorm Wind | Beechwood | $10,000 | Trees and power lines down. |
| July 2006 | Thunderstorm Wind | Cascade | $10,000 | Trees and power-lines down. |
| July 2002 | Thunderstorm Wind | Oostburg | $10,000 | no account filed |
| June 1999 | Thunderstorm Wind | Cedar Grove | $10,000 | no account filed |