There have been many tennis shots that went around the net post.
But has any tennis player ever hit a shot that went behind the umpire's chair and still landed inbounds in a singles match? There are some tennis courts that have enough space where this is theoretically possible:
I already found that it happened in a doubles match at the college level, when Gregor Ramskogler did it for Mississippi State against Tennessee on or about March 8, 2020.