Yes,
In 1997, I uncovered a flaw in chess software leading to a condition called “the thrashing syndrome”. When the player starts with one side of the board fixed, and then uses chess engines for both sides, you don’t have to do much searching at all before you find a sequence that makes an engine suffer from too much thrashing.
This isn’t possible for humans because humans actually think through the consequences of their moves whereas computers just check abstractly whether they are mates or not. So now people who play chess online using only computer programs as opponents have been winning 15-5-1 against those who also pick one human as their opponent–a result typical of what ensues when superior engines face inferior ones.