Thing One (9) has a tough time with analog clocks. They are counter-intuitive to him. He thinks the long hand should be used for the hour hand instead of the minute hand. Here are some activities I put together to try to reinforce his memorizing the rules and trying to make it fun.
Draw a huge clock outside with sidewalk chalk. Or on a dry erase board or chalkboard. Have your child hold a short stick for the hour hand and a long stick for the minute hand. You call out a time and they move their arms into the correct position.
Play this fun computer game: stop the clock.
Try time flashcards. My set has analog on one side and digital on the other. Thing Two (6) can read the digital side, too, so he can help Thing One practice.
We have found one of these to be very helpful. I love that the minutes are marked around the edges.
Here's an online one. analog clock