I did that just last week and I'm not a very technical user. I have
Daytimer version 1 from 1997 and Outlook 2002.

I followed the instructions in the articles from Daytimer and Microsoft
 (links below) and it worked!!!!

I still have lots of tweaking to do as the data was transferred, but
some of the formatting is different and many of the phone numbers are
designated wrong----labeled business when it is a home phone, for
example. And, I need to learn the intricacies in Contact to make it as
good and customizable (hopefully) as Daytimer, whioh has been a
wonderful program.

First, get the article from Daytimer with very detailed instructions.
Send an e-mail to support@daytimer.com and put the word ‘Transfer’ in
the subject field.  The automatic and immediate reply that you receive
will explain how to:
1. Transfer Day-Timer 2000 Addresses to Microsoft Outlook's Contacts folder
2. Transfer Day-Timer 2000 Schedules to Microsoft Outlook's Calendar folder
3. Transfer Day-Timer 2000 Notes to Microsoft Outlook's Notes folder
4. Transfer Day-Timer 2000 Tasks to Microsoft Outlook's Tasks folder
5. Transfer Day-Timer 2000 Addresses to ACT! 2000
6. Transfer Any Day-Timer 2000 entry type to ASCII file for import into
another program
7. Export data to a Day-Timer 2000 export file (*.exp)
8. Export data to an ASCII file
9. Import an ASCII file into Day-Timer 2000
10. Import a Day-Timer export file (*.exp) into another database on
either the same or different PC
11. Transfer all data from an old computer to a new computer
12. Backup a Day-Timer 2000 database and restore it
13. Merge (synchronize) multiple database's into one database
---------------------------------------------
http://support.microsoft.com/default.aspx?scid=kb;en-us;198395
198395 - OL2000: How to Import Day-Timer 2.0 Data Files

http://support.microsoft.com/default.aspx?scid=kb;en-us;174577
174577 - OL97: How to Import Day-Timer 2.0 Data Files into Outlook

Good luck!
Joan