I had those kind and they always leaked. The rubber insert has to be in PERFECT. No room for error or they will leak. Such a pain......

Wish I could help... I've tried most kinds of sippies and they all leak!

we use playtex and they leak all over the place- puddles everywhere! I don't think a perfect non-leaky sippy cup has been created, after they are used a few times/washed a few times it's always gamble for us.

Try one's made by Munchkin..the valve is kind of triangular in shape, love them ! Never had a leak!!

I found one at babies r us and there great. They look like regular cups and THEY DONT LEAK!!! SASSY there wonderful and they really truely dont leak. You can find them buy 1 get 1 free.

We have issues with those leaking really badly too. I actually have had good success with the cheap learning curve ones from walmart. That's about it though. They all seem to leak!

My friend introduced me to Nalgeens. They look like a sports cup but they are amazing and DO NOT leak. I thought my husband was going to loose his mind with all the leaky sippy cups but since having these, its really not an issue.

thanks everyone! Glad I'm not alone with the leaking issue.

I tried multiple cups because of this very issue and the only one I found doesn't leak is made by munchkin. It's a straw cup rather than a sippy, but I think they are by far the best, no leakage at all.

http://www.toysrus.com/product/index.jsp?productId=11016742&searchURL=true

I have the Nuby sippy cups that look very similar to yours and come with the sippy nipple and bottle kind of nipple. The bottle nipple kind has been leaking because DD bites and chews on them so much that the little tines that fold over to prevent the sippy from leaking fold back or something. Might be the same problem you are having. We have started to have to go with the hard kinds in order to prevent that.

The only sippies I have luck with..are the hard top Nuk brand..they hold up very well. The soft tip one's are awful..every time my daughter dropped one..milk would splash onto our furniture...which is still damaged..they are messy. Ive issues with so many..and the straw ones I tried were bad too..

I still am a firm believer Kala's downunder magic cups. They are so easy to put together and hold up to extreme abuse. They are expensive, but I've been using the same 4 cups for the past three years. You can even buy replacement spouts separately and they screw onto any standard sized plastic drink bottle. It's great, I bring the spouts and screw them onto water bottles if I'm out and the kiddo gets thirsty.

DD has done everything in her power to destroy them to no avail. They are still in great condition. I think the moment of truth for me was when she threw a cup at me during a tantrum. I ducked and it rebounded off of three walls without spilling a single drop. They are so sturdy, lol.