Two weeks is plenty of time. At 8.5months, I'd still wean to a bottle not a cup probably.
I did something similar at 10 months due to DD starting nursery at 10.5 months.
Sucking from a bottle is really different to sucking from a breast. I also tried lots of bottles, DD hated them all. I eventually found I needed a very fast flow teat which surprised me. I also found DD preferred the flavour of ready made cartons of milk (expensive but very convenient). So whichever approach your DD seems to hate least, go with that.
Then you just have to stick it out. Start by switching the daytime feeds, leaving bedtime and night time to last.
If your DP is able to help it would really be a good idea if, say, you do bath and cuddles and some singing or whatever is your routine, and he takes over the bedtime feed.
You'll have to be prepared for an angry, hungry baby - there isn't really a way to avoid that.
Your baby will be increasingly interested in food, make sure you offer water frequently through the day and lots of yummy things to eat. Perhaps up the dairy element of your baby's diet to compensate the loss of BF at least until bottles are established.