diff --git a/images/windows/scripts/build/Install-Selenium.ps1 b/images/windows/scripts/build/Install-Selenium.ps1
index 619cb8ffb..95aad377d 100644
--- a/images/windows/scripts/build/Install-Selenium.ps1
+++ b/images/windows/scripts/build/Install-Selenium.ps1
@@ -13,7 +13,8 @@ $seleniumMajorVersion = (Get-ToolsetContent).selenium.version
 $seleniumDownloadUrl = Resolve-GithubReleaseAssetUrl `
     -Repo "SeleniumHQ/selenium" `
     -Version "$seleniumMajorVersion.*" `
-    -Asset "selenium-server-*.jar"
+    -Asset "selenium-server-*.jar" `
+    -AllowMultipleMatches
 
 $seleniumBinPath = Join-Path $seleniumDirectory "selenium-server.jar"
 Invoke-DownloadWithRetry -Url $seleniumDownloadUrl -Path $seleniumBinPath
diff --git a/images/windows/scripts/helpers/InstallHelpers.ps1 b/images/windows/scripts/helpers/InstallHelpers.ps1
index 5bb8d87a2..a2a2341e5 100644
--- a/images/windows/scripts/helpers/InstallHelpers.ps1
+++ b/images/windows/scripts/helpers/InstallHelpers.ps1
@@ -636,6 +636,10 @@ function Resolve-GithubReleaseAssetUrl {
         The pattern to match against the download URLs of the release assets.
         Wildcards (*) can be used to match any characters.
 
+    .PARAMETER AllowMultipleMatches
+        Specifies whether to choose one of multiple assets matching the pattern or consider this behavior to be erroneous.
+        By default, multiple matches are not considered normal behavior and result in an error.
+
     .EXAMPLE
         Resolve-GithubReleaseAssetUrl -Repository "myrepo" -Version "1.0" -UrlMatchPattern "*.zip"
         Retrieves the download URL for the asset in the "myrepo" repository with version "1.0" and a file extension of ".zip".
@@ -650,7 +654,8 @@ function Resolve-GithubReleaseAssetUrl {
         [switch] $AllowPrerelease,
         [Parameter(Mandatory = $true)]
         [Alias("Pattern", "File", "Asset")]
-        [string] $UrlMatchPattern
+        [string] $UrlMatchPattern,
+        [switch] $AllowMultipleMatches = $false
     )
 
     $matchingReleases = Get-GithubReleasesByVersion `
@@ -677,9 +682,18 @@ function Resolve-GithubReleaseAssetUrl {
         Write-Debug "Found no download urls matching pattern ${UrlMatchPattern}"
         Write-Debug "Available download urls:`n$($matchingReleases.assets.browser_download_url -join "`n")"
         throw "No assets found in ${Repository} matching version `"${Version}`" and pattern `"${UrlMatchPattern}`""
-    } elseif ($matchedUrl.Count -gt 1) {
-        Write-Debug "Found multiple download urls matching pattern ${UrlMatchPattern}:`n$($matchedUrl -join "`n")"
-        throw "Multiple download urls found in ${Repository} version `"${matchedVersion}`" matching pattern `"${UrlMatchPattern}`":`n$($matchedUrl -join "`n")"
+    }
+    # If multiple urls match the pattern, sort them and take the last one
+    # Will only work with simple number series of no more than nine in a row.
+    if ($matchedUrl.Count -gt 1) {
+        if ($AllowMultipleMatches) {
+            Write-Debug "Found multiple download urls matching pattern ${UrlMatchPattern}:`n$($matchedUrl -join "`n")"
+            Write-Host "Performing sorting of urls to find the most recent version matching the pattern"
+            $matchedUrl = $matchedUrl | Sort-Object -Descending
+            $matchedUrl = $matchedUrl[0]
+        } else {
+            throw "Found multiple assets in ${Repository} matching version `"${Version}`" and pattern `"${UrlMatchPattern}`".`nAvailable assets:`n$($matchedUrl -join "`n")"
+        }
     }
 
     Write-Host "Found download url for ${Repository} version ${matchedVersion}: ${matchedUrl}"