No, on server side (does not matter the language) you can't trigger 2 different downloads in the same request.
You can do it via javascript something like the following should work:
function downloadFile(file) {
// Create a link and set the URL using `createObjectURL`
const link = document.createElement("a");
link.href = URL.createObjectURL(file);
// the link is invisible so do not show on the page
link.style.display = "none";
// this ensures the file is downloaded even if is a html one
// you can set to true, or specify with which name the file will be downloaded
link.download = file.name;
// attach to the DOM so it can be clicked
document.body.appendChild(link);
// click the link
link.click();
// this should free memory, usefull if you download many
// files without page reload
URL.revokeObjectURL(link.href);
// remove the link from the DOM
document.body.removeChild(link);
}
downloadFile('http://mywebsite/dowload/file_1.pdf');
downloadFile('http://mywebsite/dowload/file_2.docx');