The Cleveland Browns only managed to win one game last season, but it did come within their past four games played. They won the penultimate game of the 2016 season, but lost the final game, and have opened the 2017 season with a pair of losses.
In order to find the last time they won a game prior to that, you would have to go all the way back to Week 14 of the 2017 season, so they actually lost 17 consecutive games, and have only won one of their last 21 games in total, going 1-20 in that span.