I'm going to do from 2004 on.
2004 -
John Kerry/ John Edwards - 277 EV, 48.3% PV
George Bush/ Dick Cheney - 261 EV, 49.0% PV
I would have thought Kerry would pull it off, but lose the popular vote. Truly a horrible timeline here.
2008 -
Barack Obama/Joe Biden - 320 EV, 51.9% PV
John McCain/Sarah Palin - 218 EV, 46.2% PV
Honestly I would have thought McCain would have outperformed in certain areas where he didn't end up doing so, same with Obama. Overall Obama ends up losing ground but only slightly, definitely not enough to change the result of the election. I think that year I could tell it was going to be a big Democratic win anyway, but I didn't think it would be as big as it was.
2012 -
Barack Obama/ Joe Biden - 288 EV, 49.1% PV
Mitt Romney/ Paul Ryan - 250 EV, 48.8% PV
I remember this election. I was surprised how well Obama performed throughout the night, this was probably about my expectation when I sat down to watch TV that night. I thought Obama would win but also thought it would be by a much narrower margin, and would either lose or come close to losing the popular vote to Romney.
2016 -
Hillary Clinton/Tim Kaine - 324 EV, 48.9% PV
Donald Trump/Mike Pence - 214 EV, 45.3% PV
I expected a Clinton win that night, which is why I went to bed at like 10 PM pretty confident that Trump was going to win, because even by that point Trump was over performing everywhere where I thought Clinton needed to win, as well as much lower turnout than 2012. When I woke up at 4 AM and looked at my phone to check the time and the results I was proven right about my earlier feeling.