Here is the multiple file upload version:
Cypress.Commands.add('uploadMultiFiles',(args) => {
  const { dataJson, dirName, inputTag, mineType} = args
  const arr = []
  dataJson.files.forEach((file, i) => {
    cy.fixture(`${ dirName + file }`).as(`file${i}`)
  })
  cy.get(`${inputTag}`).then(function (el) {
    for(const prop in this) {
      if (prop.includes("file")) {
        arr.push(this[prop])
      }
    }
    const list = new DataTransfer()
  
    dataJson.files.forEach((item, i) => {
      // convert the logo base64 string to a blob
      const blob = Cypress.Blob.base64StringToBlob(arr[i], mineType)
  
      const file = new FileCopy([blob], `${item}`, { type: mineType }, `${ dirName + item }`)
      const pathName = dirName.slice(1)
      file.webkitRelativePath = `${ pathName + item}`
      console.log(file)
      list.items.add(file)
    })
  
    const myFileList = list.files
    
    el[0].files = myFileList
    el[0].dispatchEvent(new Event('change', { bubbles: true }))
  })
})
The usage:
First, prepare a data.json file inside the fixtures folder, example:
data.json
{
  "files":[
    "1_TEST-JOHN-01.jpeg",
    "2_TEST-JOHN-01.jpeg",
    "3_TEST-JOHN-01.jpeg",
    "4_TEST-JOHN-01.jpeg",
    "5_TEST-JOHN-01.jpeg",
    "6_TEST-JOHN-01.jpeg",
    "7_TEST-JOHN-01.jpeg",
    "8_TEST-JOHN-01.jpeg",
    "9_TEST-JOHN-01.jpeg",
    "10_TEST-JOHN-01.jpeg"
  ]
}
Second, import the json data into your spec.js
import data from '../fixtures/data.json'
Third, Write a class to extend the File web API object with the functions to set and get webkitRelativePath value
class FileCopy extends File {
  constructor(bits, filename, options) {
    super(bits, filename, options)
    let webkitRelativePath
    Object.defineProperties(this, {
        webkitRelativePath : {
            enumerable : true,
            set : function(value){
                webkitRelativePath = value;
            },
            get : function(){
                return webkitRelativePath;
            } 
        },
    });
  }
}
Finally, call the cmd in the spec.js
cy.uploadMultiFiles(
      {
        dataJson:data, // the data.json you imported.
        dirName:"/your/dirname/",
        inputTag:"input#upload",
        mineType:"image/jpeg"
      }
    )