A common situation where something like this can happen is in batting averages. It’s a question of weighted averages. The sum total of my knowledge of baseball boils down to: The season is split in half by the All Star Break. This is probably not even true, but it doesn’t matter. 
So we have two batters. In the first half of the season, batter A has a better average than batter B. In the second half of the season batter A has a better average than batter B. Over the season as a whole, batter B has a better average than batter A. How can this happen? Here’s an extreme case:
1st half: Batter A gets up to bat, hits a home run. This is the first game of the season. At his next at bat he throws out his back swinging for the fences and doesn’t ever come up to bat until after the break. His average? .500
1st half: Batter B has a great start to the season, he comes to bat 100 times and hits safely 34 of them. His average is .340
2nd half: Batter A is off the disabled list and comes to bat 100 times. He hits safely 25 of those times and so has an average of .250. This is still pretty good.
2nd half: Batter B is tired from going so gangbusters in the first half and only bats 10 times. He only gets 1 hit and retires in disgrace. Effigies are burned and his children never show their faces in public again, so ashamed are they of his pathetic .100 batting average.
Over the course of the whole season? Batter A has 102 at bats and 26 hits for an average of .254 which is a respectable number. Batter B has 110 at bats and 35 hits. His average is .318. Oops.
As I understand it, this type of thing happens fairly often in baseball. Some players play more at the beginning of the season and then get hurt or whatnot and so play less. Other players really step it up at the end of the season when playoff time starts getting close. Because they play different numbers of games in the different seasons, the averages do counterintuitive things.
Another example is alcoholic content in drinks. Bacardi is 40% alcohol while Malibu is only 20%. Everclear is 95% alcohol while 151 is 75%. If you take a bottle of Bacardi and put in a splash of everclear you get something with less punch than a bottle of 151 with a splash of Malibu, even though Bacardi is stronger than Malibu and Everclear is stronger than 151.
By the way, you shouldn’t make any of these conconctions because they’d be gross. And you’ll probably go blind.