Junior Career
Bob and Mike won their first doubles tournament at age 6, in a 10-and-under event. They had an outstanding junior career, winning well over a hundred junior doubles titles together. They won the 1991 USTA National Boys' 14 Doubles Championships, the 1992 USTA National Boys' 14 Clay Court doubles title, the 1994 USTA National Boys' 16 Clay Court doubles title, the 1995 USTA National Boys' 18 Clay Courts doubles title, the junior doubles title at the 1995 Ojai Valley, California Tennis Tournament, and the first-ever Easter Bowl boys' 18 doubles title.
The brothers won the USTA National Boys' 18 Clay Court Championships again in 1996, becoming the first team in 30 years to repeat as doubles champions at that event. Bob and Mike became the first repeat doubles champions in 50 years at the 1996 USTA National Boys' 18 Championships in Kalamazoo, Michigan, defeating Michael Russell and Kevin Kim in the final.
The Bryans then won the 1996 US Open junior boys' doubles title, defeating Daniele Bracciali of Italy and Jocelyn Robichaud of Canada 5–7, 6–3, 6–4 in the final. They went on to win the bronze medal at the 1999 Pan American Games at Winnipeg, Manitoba, Canada, where they represented the United States for the first time as professionals.
They attended Mesa Union School in Somis, California, for elementary and junior high school, then attended Rio Mesa High School in Oxnard, California. Both brothers were awarded full-ride tennis scholarships to Stanford University in fall 1996, and played there through 1998, helping the team to NCAA team title both years. They won the NCAA doubles title in 1998, defeating Kelly Gullet and Robert Lindstedt of Pepperdine University in the final, becoming the first brothers to win the NCAA doubles title since Robert and Tom Falkenberg of USC in 1946. They finished the year ranked No. 1 in the collegiate doubles rankings.
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