Here's a win from Christmas Eve 1986 (#6313D) during the four digit era. The contestant kept screwing up the first line, so the audience had to help her.
Here is proof of Jacqueline’s epic fail in One Away (#7691D). As Bob says, the car was a Lincoln, which nowadays doesn't cost anywhere near $10,000.
Here's better news. This is how you win One Away from October 20, 1997 (#0491K).
Here's another win between 2003-2006.
O mighty sound effects lady, do I have at least one number right?