It may be a bit babyish for him, but the playschool site on ABC kids has a tell the time with Jemima game that deals with Jemima's day and the time and the clock when she does things.
We will be using the analogue clock again with DS2 - I work at Parliament House and with over 2700 clocks in the building he quickly learnt what a "clock" was!
With DS1 I actually found it easier with analogue. I bought him a watch that had "quarter past" and "quarter to" and "half past" etc. You can buy "clock face" online from ELC toys dot com dot au - they're only $5.
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