You would have to run 5 separate scripts in parallel.
You can use a batch file like this:
start "" winscp.com /command "open FTPSERVER" "D:\1.ZIP" "exit"
start "" winscp.com /command "open FTPSERVER" "D:\2.ZIP" "exit"
start "" winscp.com /command "open FTPSERVER" "D:\3.ZIP" "exit"
start "" winscp.com /command "open FTPSERVER" "D:\4.ZIP" "exit"
start "" winscp.com /command "open FTPSERVER" "D:\5.ZIP" "exit"
Though note that 5 parallel uploads are too much, that will hardly give you a better performance than 2-3.
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For a different implementation, see:
https://winscp.net/eng/docs/library_example_parallel_transfers