My 2 cents worth! I live in an area where lots of row crops are raised and irrigated.
First ditch the thoughts of ‘level’! A level has its place, but when speaking of land the terminology is ‘grade’! In roof construction ‘pitch’ and so forth.
With grade in mine if your tractor is on a grade then do is your BB. When you change your tilt, you change your grade! (You may increase the grade or decrease the grade compared to your tractor.)
From living in other areas, any preexisting slope of the land is a bear to redirect water flow. It can be done but be prepared for it to take lots of correction.
I am sure you have areas of your drive that are worse, these will be the most difficult to correct in my opinion and thus the most frustrating to work.
I suggest studying these areas to get a feel for how water wants to flow, then patch these spots up. Go to less washout areas and apply what you learned from studying the worse areas. Then from notes evaluate your work on the less troublesome areas to see what worked and what did not.
Changing water flow is one of the toughest projects I think exist.
Also work small areas and mark them for your notes in some manner.
And in my opinion a football field length is mot a small area. It may be nothing to your drive, but for water flow, you may have a dozen or more issues happening. 2-3 issues is plenty when trying to control water flow. Also if possible work from the high end to the low end of water flow.
Good luck it is a challenge.