The Election of 1828
The parallels of Andrew Jackson and John Quincy Adams with current events are eerie. Here you have a well known demagogue known for his rash decisions and short temper promising to make America great again paired with an extremely well-educated Senator and Secretary of State with family ties to the Presidency. Just remarkable.
Andrew Jackson was a fan of making his candidacy about being the one for the people, while trying to ignore his past of getting into brawls, gambling, and problems with women. Alternatively, John Quincy Adams was often criticized for lacking the charisma of his father, John Adams, and accused of political corruption.
I will note that there was no formal debate between these two, but their mudslinging write-ups in the print media were just as petty and hostile as you would see in an actual debate today.