"Move mouse to text on screen (OCR)"...seems like it is every seven days, so you should bable to calculate the Check Date (I wouldn't use settlement date as it appears in the settlement date and the previous check date. So for this instance, you would say:

You could replace 10/29/2021 with a variable that is calculated elsewhere. And the Offset of X where I have 300, should be however many pixels it takes to get from the center of the date field to the center of the link to click.
Whether you decide to do this in a loop or write each out separately, the second time will have to change the "Occurrence" number to "2".
Start with trying to extract the text from the page, and make sure you are getting valid OCR readings. If not, go to OCR engine settings and start adding one to each multiplier until you get a proper OCR reading. The higher the number, the longer it takes to OCR the screen; however, each number is increasingly more accurate.

If you are having trouble knowing how many pixels to offset, open a "Move mouse" command, and it will show the current location of your mouse. Get the link coordinates and the date coordinates and subtract the X amounts to get your offset.
Best of Luck!