Before turning pro, Chrystal was a key member of the Brandon Wheat Kings of the Manitoba Junior League, twice appearing in the Memorial Cup, including in 1949 when they lost a heart-breaker to the Montreal Royals.
After his junior career Chrystal spent a year in the USHL with Denver before spending two seasons with the AHL Cleveland Barons. After his two years with Cleveland he was traded to the NHL Rangers.
After his two year stint in the Big Apple concluded, Chrystal returned to the Canadian prairie and the old Western (professional) Hockey League. After a year with the Saskatoon Quakers he returned to Brandon to play with the Regals. Unfortunately the Regals moved to Saskatchewan and later St. Paul, Minnesota, so Bob's homecoming was short though sweet.
In 1958-59 Chrystal played his final season of serious hockey in his hometown with the Winnipeg Warriors.