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The phrase "several times when" is correct and usable in written English
You can use it when you are referring to multiple, distinct occasions when something has occurred. For example: "He had asked me several times when I would be able to come over."
Exact(56)
The fire alarm went off several times when there was no fire.
He frowned, several times, when the 49ers fell behind by 17 points early.
"Several times when I visited him, he said, 'They're not feeding me,' " the brother told me.
Still, there are some lovely moments, including several times when characters sing carols or folk songs.
I had to get her cellphone from her house several times when she left it there".
The music business was sagging badly (as it had several times) when "Thriller" came along.
"We had the same discussion several times when someone would die," Phelps-Roper said.
Mr. Korzun recounted several times when teams competing in foreign countries were presented with culinary challenges.
Several times when the woman was questioned, officials say, her story changed.
I interviewed Yasir Arafat several times when the United States considered him a notorious terrorist.
There were several times when I would throw up before school.
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Since I tried Ludwig back in 2017, I have been constantly using it in both editing and translation. Ever since, I suggest it to my translators at ProSciEditing.

Justyna Jupowicz-Kozak
CEO of Professional Science Editing for Scientists @ prosciediting.com