Given what we know about when the wins have happened, the best 162 game span is going to be some time in 2015 through a similar spot in 2016. The 2015 Cubs took off in July and the 2016 Cubs slumped in late June/early July, so that narrows it down further. The 2016 slide started after 67 games, so if we back up 95 games into 2015 we get a 60-35 stretch to end 2015, and 47-20 to start 2016, or a 107 win pace. If you want to cherry pick a bit more, the 2016 Cubs were 39-15 to start the year, and the 2015 Cubs ended winning 45 of their last 63. That gives a consecutive span of 84-33 over 117 games, which is a 116 win pace per 162 games. Numbers look right but I figured a 104 win team would have a better rolling 162 than 107 wins. Only 3 better than they actually had. Any chance there was a stretch after the Cubs slide but back when they got hot again that rolled better than 107? Didnt we have another smoking stretch late july to aug of 2016. That would still roll back through the super hot 2015 end anx start of 2016 too? Let's see! Using that 45-18 stretch to close 2015, you can tack on the 59-40 start to 2016 but only get to 104 wins. The 2016 Cubs at one point were 82-45, which combined with the 2015 Cubs finishing 24-11 only gets up to 106. It's just a really tough combo to find a streak in. The 2016 Cubs started so white hot, and 1/3 of their losses came in a one month span right in the middle of the season, and the 2017 Cubs didn't start out super hot, that it's difficult to find something much better than these 106 and 107 game stretches. Quite possible I'm missing something though. Wait here's one more, the 2015 Cubs closed the year 21-7, and the 2016 Cubs started 87-47, which gets us to 108 as a rolling 162 game stretch. Not what you're hoping for, but the best yet I've found.