Livvy,
I just wanted to chip in and tell you that when I went back to work after DS he was 6 months old. I just went straight to a sippy cup. But I didn't start offering it until around 5 months. We used Avent cups and had the bottles though had rarely used them so he did not drink much from the bottle. For the first couple of weeks I sent sippy spouts and bottle teats to nursery - mainly in case they needed to comfort him to sleep. However, they never needed to use the teats. Fraser had taken (or been offered) a bottle maybe 3-5 times so there was never any major transition from bottle to cup, just breast to cup.
We combined sippy's of my milk at nursery and breastfeeding all the rest of time until he was over a year. I worked pretty long days (commutting

) so he generally had a feed first thing, last thing and one night-waking, so even on days when he did not take all his milk at nursery he seemed to do OK. I only worked M-W and exclusively breastfed the rest of the time, so we always had mini-growth spurts on Thursday mornings where we would fit in an extra feed or two.
I hope it all goes well for you.