You were the closest to the date of manufacture for the prize watch.
The correct answer is: JUNE 1990
The date code on the case back is "66". Check the link below to the Date Code Chart:
TIMEX QUARTZ DATE CODE CHART
Mark's entry was OCTOBER 1988, which was the closest to the exact date.
Mark, please email me your mailing address and I'll get the watch in the mail to you ASAP.
CONGRATULATIONS MARK!
Cheers, 
Ed
Visit my website:
EdHeffington.com