4th times the charm?

In the finale, the team mentions this would be the 4th time Selina runs for president. There was her primary where she lost to Hughes, the election tie and now this? It's driving me crazy what the other time is.

Also, is it technically 2019 in the show? This season started a year after the vote and then a significant amount of time has passed so I guess we are in 2019 prepping for 2020? If only real life politics moved that quickly.