Playing Medleys

Is there anyway that I can make both iTunes and my iPhone play medleys in order?

For example the Abbey Road Medley or Sgt. Pepper's Lonely Heart Club Band medley.

I want to be able to play the Abbey Road medley(the side b) of the album while in shuffle mode. I've already grouped the songs into an "Abbey Road Medley" group but after the first song in the medley finishes it completely goes to a different song not part of the medley.

Any help is appreciated. Please and Thank You! 🙂