| May 1999 | Thunderstorm Wind | Orangeville | 1 hurt, $40,000 | Severe thunderstorm winds rolled a mobile home trailer over and destroyed it. The occupant of the trailer suffered 2 dislocated shoulders, cuts, and abrasions. |
| July 2008 | Thunderstorm Wind | Winslow | 1 hurt, $25,000 | Wind gusts estimated to be 70 mph blew down a pole barn on State Line Rd and Swiss Rd near Winslow, IL at 12:35 pm July 31. One person was injured with several fractures. |
| July 2003 | Thunderstorm Wind | Pearl City | 1 hurt, $20,000 | Limb down on a tent |
| August 1987 | Thunderstorm Wind | not stated | 1 hurt | no account filed |
| July 2017 | Flood | Winslow | $7,000,000 | Heavy rainfall of 3 to over 12 inches over significant areas from 20 to 22 July in southern Wisconsin and Northern Illinois moved downstream causing the Rock River to rise well above major flood stage levels just downstream of Freeport down to the Mississippi at Moline. ||Freeport rose just below major flood stage level of 16.0 feet on July 23rd, 2017 at approximately 645 AM CST. It crested around 15.9 feet at approximately 10 AM CST on July 23rd, 2017 and fell below 15.5 feet at approximately 815 PM CST on July 25th.||Widespread river flooding and flash flooding resulted in a preliminary estimation of 7 to 8 million dollars in damage. |
| July 2003 | Thunderstorm Wind | Countywide | $2,500,000 | Numerous trees & power lines down |
| October 1958 | Tornado (F2) | not stated | $2,500,000 | no account filed |
| April 1996 | Thunderstorm Wind | Pearl City | $1,200,000 | no account filed |
| July 2010 | Flash Flood | Waddams Grove | $1,000,000 | Heavy rains of 2.5 to 6 inches fell across Stephenson County the evening hours of July 22 and through the morning of July 23 resulting in flash flooding of much of the county. At 1248 am CDT, Freeport was flooded with about 10 inches of water in the streets. Several roads were completely covered with water, especially in the vicinity of the Taylor Park District and near Route 75. The flood waters came up to the middle of car tires. Just before 130 am CDT, WREX TV relayed a report from a Freeport viewer that there was standing water everywhere. At 405 am CDT, several homes in Pearl City were flooded. Some of the residences on the north side of town had flood waters up to the first floor level. In addition, the city's sewer system was overwhelmed with the flood waters blowing some manhole covers off. Route 73 near Pearl City was closed due to 8 inches of water flowing across the road, and Yellow Creek began flooding some nearby homes. Highway 26 just south of Freeport was also closed due to flooding. Trained spotters, CO-OP observers, the general public, WREX TV, and emergency management all contributed to this report. |
| July 2011 | Flash Flood | Waddams Grove | $500,000 | Torrential rains of 3 to 8 inches caused some flash flooding across parts of Stephenson County during the evening of July 27 and morning of July 28. There were reports of cattle scattered through county by flood waters with some washed downstream. The flood waters were several feet deep in the town of Pearl City. Two people died just west of Freeport, IL from carbon monoxide fumes from a generator use to pump water from a flooded basement. |
| July 2010 | Flash Flood | Winneshiek | $500,000 | Heavy rains of about 3 inches in under 3 hours (for a total of about 11 inches in less than 32 hours) resulted in extensive flash flooding during the morning of July 24. The greatest impact was flash flooding of Yellow Creek from Pearl City to Freeport, with additional impacts from flash flooding of the Pecatonica River in and near Freeport. ||Local emergency management officials described the flood damage as the worst damage I've seen in 19 years, and many lifelong residents affected by Yellow Creek described it as worse than anything they had ever experienced in their lifetimes. ||Forty-three roads in Stephenson County were under water and closed to traffic, including Business Highway 20, Highway 20, and Route 75. Streets in downtown Freeport had as much as 5 to 6 feet of water. Some people who were trapped in flooded vehicles were rescued by boat. In the weeks following the flash flood, more than 20 sink holes developed in Freeport roads. The Stephenson County engineer documented about $1 million in damage to county and township roads.||In Pearl City, about 80 homes were damaged in the flooding of Yellow Creek, and an additional 60 homes in unincorporated portions of the county we also damaged. One Pearl City resident awoke around 3 am CDT to the sound of trickling water to discover his possessions floating in 3 feet of water.||More than 700 homes and countless businesses in Freeport were damaged. Numerous stores in the Southgate Market area were flooded and remained closed for at least 2 weeks, some for as long as 6 weeks. Also affected was the Winneshiek Playhouse, the oldest amateur theater in the United States, which suffered 3 feet of water in its basement. Freeport Fire Station 3 was nearly completely under water and was evacuated due to the flooding. Due to repeated rounds of heavy rain (with nearly a foot of rain measured in less than 48 hours), the Freeport wastewater treatment plant sustained about $1.4 million in damages. |
| July 2010 | Flood | Winslow | $500,000 | no account filed |
| August 2008 | Thunderstorm Wind | Freeport | $250,000 | Wind gusts estimated to be 65 to 75 mph caused widespread tree and structural damage in the vicinity of Freeport, IL between 630 pm and 655 pm August 4. On Rock City Rd, several trees and branches were blown down as well as a metal storage shed. In addition, twenty-five rows of corn on both sides of the road were flattened. Some buildings on the southwest side of town were damaged. On Fairview Rd, a tree was blown over onto a house. On Edwardsville Rd, some large tree limbs were blown down. A power outage was also observed across the county. |
| June 1971 | Tornado (F1) | not stated | $250,000 | no account filed |
| July 2003 | Thunderstorm Wind | Freeport | $150,000 | Mobile home overturned & limbs down |
| April 2010 | Thunderstorm Wind | Freeport | $100,000 | Wind gusts estimated to be 70 mph snapped some trees and utility poles in half and ripped some siding off of some houses along Pearl City Rd about 0.25 miles west of Highland Community College on the west side of Freeport, IL around 1155 pm April 5. This report was relayed by Stephenson County SKYNET. In addition, a 40 foot tall pine tree on the 1200 block of Lincoln Boulevard fell onto a house. Several Freeport streets were littered with downed trees, especially hard hit were South High Ave, Lemon Ave, Nursery Ave, Bauch Ave, West Pleasant St, and South Highland Ave. The Freeport Journal Standard also contributed to this report. |
| June 2009 | Thunderstorm Wind | Buena Vista | $100,000 | Wind gusts estimated to be 70 mph blew some farm equipment over in a nearby farm field about 3.5 miles southwest of Orangeville, IL around 430 pm June 1. The equipment was laying to the south. It was determined that downburst winds caused this damage. Time estimated. |
| June 2009 | Tornado (EF0) | Buena Vista | $100,000 | A tornado briefly touched down about 2 miles southwest of Orangeville, IL around 430 pm June 1. Several trees were snapped at the trunk. Tall grasses along W Brush Creek Rd were laying down to the east. A tin roof was blown off of a shed to the east. A witness inside a barn described windows blown in, paint sandblasted off walls, and hay blowing out the west door being carried north of barn. An empty grain wagon was pushed 25 yards northeast of barn. Four calf huts were picked up by the wind, moved, and one was apparently lofted a half mile down the road to the northeast. Sheet metal was bent and twisted inside a grain bin. A hay conveyor rolled twice. A witness described heavy rain, then mud preceding wind. Another witness described seeing a funnel cloud shape before experiencing strong winds. They were unable to determine if there was rotation due to the wind speed and rain. A pine tree was uprooted along with small branches down. Time estimated. |
| August 1998 | Tornado (F1) | Pearl City | $80,000 | no account filed |
| August 2010 | Thunderstorm Wind | Freeport | $50,000 | Wind gusts estimated to be 65 mph blew a limb down in Freeport, IL around 255 pm CDT August 20. The limb, which was 6 to 8 inches in diameter, fell onto some power lines which in turn caused a house fire. This report was relayed by WREX. |
| July 2009 | Hail | Kent | $50,000 | Hail estimated to be 2 inches in diameter fell about 1.5 miles north northeast of Kent, IL around 615 pm July 24. The hail caused widespread crop damage as well as damage to some residences and vehicles in the area. |
| July 2008 | Thunderstorm Wind | Lena | $50,000 | Wind gusts estimated to be 65 mph blew down four utility poles near the intersection of N 5 Corners Rd and Highway 20 about 2 miles south southwest of Lena, IL around 9:30 pm July 7. A power outage was observed in several surrounding communities. This report was relayed by the Freeport Journal Standard newspaper. |
| July 2003 | Thunderstorm Wind | Freeport | $50,000 | 8 inch limbs down |
| September 2000 | Lightning | Lena | $30,000 | Lightning struck a home and ignited a fire. |
| May 2011 | Thunderstorm Wind | Ridott | $25,000 | Wind gusts estimated to be 70 mph snapped some trees in half, blew down some power poles, and damaged a cattle barn and a pole barn near the intersection of Highway 20 and Farwell Bridge Rd about 2 miles east of Ridott, IL around 640 pm CDT May 22. |
| June 2009 | Lightning | Freeport | $25,000 | Lightning struck a Church in Freeport, IL around 945 am June 19. |
| June 2008 | Thunderstorm Wind | Freeport | $25,000 | Wind gusts estimated to be 65 mph blew down some 12 inch diameter tree limbs and caused structural damage to some buildings along Highway 20 south of Freeport, IL around 3:10 pm June 12. |
| August 2003 | Hail | Freeport | $25,000 | no account filed |
| April 1959 | Tornado (F1) | not stated | $25,000 | no account filed |
| September 2005 | Thunderstorm Wind | Freeport | $20,000 | 1 to 3 foot diameter trees were downed during a downburst on the north side of Freeport. One tree fell on a house causing unspecified damage. The Stephenson County Emergency Manager measured 48 knot (55 mph) winds 1 mile south of Freeport. The Freeport Albertus Airport (KFEP) further south of the city measured 46 knot winds during the 1615-1625 CST (2215-2225 UTC) time period. |
| June 2004 | Flash Flood | Cedarville | $20,000 | Culvert washed out on Scioto Mills Rd between Beaver and Cedarville Rds. |
| August 2003 | Hail | Kent | $20,000 | no account filed |
| August 2003 | Hail | Eleroy | $20,000 | no account filed |
| June 2009 | Thunderstorm Wind | Buena Vista | $15,000 | A large tree branch fell down on car about 1 mile southwest of Orangeville, IL around 430 pm June 1. A witness reported very heavy rain with about a 20 second long duration of high winds. There was a lot of scattered small debris mixed in with the rain and wind that sounded like popcorn hitting the side of the house. It was determined that this damage was caused by stright-line winds. Time estimated. |
| June 2008 | Thunderstorm Wind | Winslow | $15,000 | Winds estimated to be 65 mph blew down several trees in Winslow, IL at 10:15 am June 8. The trees knocked down numerous power lines resulting in a power outage to part of Winslow. |
| June 2008 | Thunderstorm Wind | Freeport | $15,000 | Winds estimated to be 65 mph blew down several large tree limbs down onto power lines in Freeport, IL at 10:20 am June 8. A power outage resulted affecting a part of Freeport. The tree limbs were over six inches in diameter. |
| June 2008 | Thunderstorm Wind | Freeport | $15,000 | Winds estimated to be 65 mph blew down several trees onto power lines just southwest of Freeport, IL at 10:20 am June 8. A power outage resulted affecting a part of Freeport. |
| June 2008 | Thunderstorm Wind | Winneshiek | $15,000 | Winds estimated to be 70 mph blew down several trees onto power lines along North Dakota Road or about 4 miles northeast of Freeport, IL at 10:30 am June 8. A power outage was also reported. |
| July 2003 | Heavy Rain | Pearl City | $15,000 | Ditches full. Some erosion along edges of Pearl City to Elroy Rd. |
| May 1999 | Thunderstorm Wind | Freeport | $15,000 | Severe thunderstorm winds downed trees and power lines from Freeport through Cedarville to Rock Grove, including several at the Cedarville Cemetery. Some trees fell onto and blocked Highway 26. At the Dornink Airport in rural Cedarville, 2 hangars were destroyed and a third hangar lost its roof. |
| July 2003 | Hail | Rock City | $15,000 | no account filed |
| August 2018 | Lightning | Ridott Corners | $10,000 | A public report of a barn fire caused by lightning. |
| June 2010 | Thunderstorm Wind | Freeport | $10,000 | Trees and power lines were downed by severe thunderstorm wind. |
| June 2010 | Thunderstorm Wind | Pearl City | $10,000 | Wind gusts estimated to be 70 mph blew down several trees and wires in Pearl City, IL around 230 pm June 18. This report was relayed by emergency management. |
| August 2007 | Flash Flood | Lena | $10,000 | Heavy rains of 3 to 7 inches fell across Stephenson County during the early morning hours of August 7th resulting in flash flooding. Two feet of water was coving parts of Highway 20 east of Highway 73. Some motorists were stranded in high water in Freeport, IL. Several gravel roads east of the Highway 20 and Highway 73 intersection were washed out. The US Bank and Health Department buildings in Freeport had flooded basements. |
| June 2004 | Flash Flood | Lena | $10,000 | Yellow Creek out of banks; Sunnyside Rd closed due to high water. |
| June 2004 | Flash Flood | Lena | $10,000 | Wagner Rd closed due to high water. |
| June 2004 | Flash Flood | Lena | $10,000 | Waddams Creek out of banks; Jct of Unity and Louisa Rds closed due to high water |
| April 2004 | Thunderstorm Wind | Winslow | $10,000 | no account filed |
| August 2003 | Hail | Pearl City | $10,000 | no account filed |
| August 2003 | Hail | Kent | $10,000 | no account filed |
| August 2003 | Hail | Cedarville | $10,000 | no account filed |
| August 2003 | Hail | Kent | $10,000 | no account filed |
| June 2005 | Thunderstorm Wind | Lena | $8,000 | Tree down on a house; power lines down in city. |
| May 1999 | Thunderstorm Wind | Freeport | $8,000 | Severe thunderstorm winds downed 8 trees and a traffic signal. |
| June 2011 | Thunderstorm Wind | Rock City | $5,000 | Wind gusts estimated to be 60 mph downed some power lines onto Highway 75 near Rock City, IL at 954 pm CDT June 8. This report was relayed by the media. |
| July 2009 | Thunderstorm Wind | Pearl City | $5,000 | Wind gusts estimated to be 70 mph broke a telephone pole near the intersection of Pearl City Road and Mill Grove Road about 1 mile east of Pearl City, IL around 633 pm July 24. |
| July 2009 | Flash Flood | Freeport | $5,000 | Heavy rains caused some flash flooding of some streets in Freeport, IL during the late evening hours of July 27. Several traffic signals were disabled. |
| June 2008 | Thunderstorm Wind | Pearl City | $5,000 | Wind gusts estimated to be 60 mph blew some tree limbs down onto some wires along Goldmine Road near Pearl City, IL at 10:50 pm June 12. |
| August 2008 | Thunderstorm Wind | Freeport | $5,000 | Wind gusts estimated to be 65 mph blew down several trees up to a foot in diameter 1 mile east of Freeport, IL at 630 am August 4. In addition, power lines were knocked down. |