I have a file that has the following below, I am trying to remove everything from <!-- to -->
<!--<br>
/* Font Definitions */
-->
Only keep this part 
I have a file that has the following below, I am trying to remove everything from <!-- to -->
<!--<br>
/* Font Definitions */
-->
Only keep this part 
Don't use a regex. HTML isn't a regular language, so it can't be properly parsed with a regex. It will succeed most of the time, but other times will fail. Spectacularly.
I recommend cracking open the file, and reading it a character at at time, looking for the characters <, !, -, followed by -. Then, continue reading until you find -, -, !, followed by >.
$chars = [IO.File]::ReadAllText( $path ).ToCharArray()
$newFileContent = New-Object 'Text.StringBuilder'
for( $i = 0; $i -lt $chars.Length; ++$i )
{
    if( $inComment )
    {
        if( $chars[$i] -eq '-' -and $chars[$i+1] -eq '-' -and $chars[$i+2] -eq '!' -and $chars[$i+3] -eq '>' )
        {
            $inComment = $false
            $i += 4
        }
        continue
    }
    if( $chars[$i] -eq '<' -and $chars[$i+1] -eq '!' -and $chars[$i+2] -eq '-' -and $chars[$i+3] -eq '-' )
    {
        $inComment = $true
        $i += 4
        continue
    }
    $newFileContent.Append( $chars[$i] )
}
$newFileContent.ToString() | Set-Content -Path $path
Regular expressions to the rescue again -
@'
<!--<br>
/* Font Definitions */
-->
Only keep this part 
'@ -replace '(?s)<!--(.+?)-->', ''
(?s) makes dot match new lines :)