His first weekend in the show ring, when he was 7 months old, Duncan won his class at Montgomery County under breeder-judge Ms. Peggy Haas with Randell Dickerson at the lead.

In November of 1999, when Duncan was 8 months old, he and Randell made their first Texas appearance together at Fort Bend Kennel Club Inc. in Katy, TX. Duncan got his first major that weekend, winning Terrier Group One from Mr. Jon R. Cole (pictured left) and Terrier Group Two from Mr. Yoshio Mori (right).

In March of 2000, Duncan won Best Of Winners and Best Of Opposite Sex from breeder-judge
Ms. Georgia Harris at the WHWTC Of Southeast Texas Specialty (pictured left). This win gave Duncan his second major. The following week, during the Trinity Valley WHWTC Specialty weekend, Duncan earned his third major and his Championship at Texas Kennel Club, Inc. (right). Ms. Martha M. Olmos-Ollivier awarded him Winners Dog and Best Of Opposite Sex over top-ranked Westie Champions.