Winnie and Kevin did not end up together. Near the end of the episode (in a voice over I think) it says that he and his wife had gone to the airport to pick up Winnie who had been living in France (studying art????). As to whether they 'sealed the deal' it was never exactly said, I think the viewers were supposed to decide if it was something that they had wanted to happen.
I am a geek... I remember this from the original showing.