Can't really comment when it comes to sports-AH, but I do think you analogise this more widely. Simply put, there's no interest in the story if all you do is flick every switch so what went 'wrong' now goes 'right' for the loser.
So if you look at Anne Somerset's essay on the Spanish Armada, she starts off reasonably (the experienced Marquis de Santa Cruz does not die leaving command to the Duke of Medina Sidonia who had little naval experience), then just starts getting silly. Drake's schemes fail. Santa Cruz anticipates the possibility of fire ships. The Duke of Parma suddenly has no logistical issues and loads an army in 72 hours he couldn't manage to embark in over a week historically. The Dutch decide not to attempt an attack on the vulnerable Spanish troops while they're crossing the channel and just let the invasion happen while not caring (later the conquest of England leads them to just give up on independence and become Good Catholic Spanish Subjects again). The English army is just brushed aside and Elizabeth calmly submits to being arrested and imprisoned rather than attempting to flee to exile or even retreat out of the London area. England calmly accepts Philip as King and a Spanish Infanta as governor and then James VI of Scotland just converts to Catholicism and brings the rest of Scotland with him.
Not only does it manage to make the Spanish Armada appear impossible to have even remotely succeeded because so much appears to need to go right for it to happen, it's also so blatantly 'Phillip II of Spain's wishful daydream' that its just dull.