How can I sync outlook 2003 contacts and calendars to icloud?

You really need to attend some reading comprehension classes before you post. I am not the one proposing the use of Outlook 2003.

For whatever reason, I can sync (wirelessly) my outlook 2003 calendar to my iphone 5 and ipad 2. I do not know why it works. My friend has the same set up and it will not work for him. I have tried to figure out what is different on my computer but so far nothing has turned up.

Outlook 2003 and iCloud are not compatible, ask your friend how he is managing it.

Akaelsie, are you syncing with iTunes? I'm just catching onto this whole Apple world and have recently discovered that syncing should be done with iTunes OR iCloud but not both. I sync my iPhone and iPad with Outlook via iTunes. Not as convenient as the automatic syncing with iCloud (I assume its automatic but I don't use it) but it does work and its great to be able to work with my calendars on my desktop or remotely. I just try to get in the habit of syncing every day, but the wireless sync to iTunes is pretty convenient. You need to be careful if you selected icloud on your portable device because if you turn off icloud it will ask if you want to merge or delete your icloud version. I think I merged once when I was playing around iwth icloud and duplcated all my contacts. just now I turned it on trying to use icloud syncing with my calendar and couldn't get it to work with outllook 2003 so I turned off syncing with icloud on my phone and ipad but deleted the calendar on the phone and ipad. Then i went into itunes and selected my ipad, then the info tab, and then at the bottom, "Advanced" has an option to replace info on the phone (or ipad) during the next sync. So I checked that, picked Apply and voila, my outlook calendar is back on the phone and ipad. To be safe before I started messing with any of this i synced all three and then backed up my outlook data.

I solved by creating an account on outlook.com.

Using this for the calendar only (so far) it can be read by outlook2003 and by iCal.

Requires a download of an addon for outlook etc but it is all quite easy.

Incidentally ignore morons like flexcrush. He is clealy a tosser. For our US readers that means he is 14 years old, knows it all, and has just found a brand new toy in his underpants.