Kiprusoff moved to North America in 1999, joining the Sharks' AHL affiliate, the Kentucky Thoroughblades. He finished fourth in the League with a 2.48 GAA and was the starting goaltender for team PlanetUSA at the 2000 AHL All-Star Game as he helped Kentucky win its first division title. He began the 2000–01 season with Kentucky, where he posted a record of 19–9–6 with two shutouts in 39 games. He then started his second-consecutive AHL All-Star Game before earning a call-up to San Jose on March 5, 2001. He earned his first NHL win on March 29, 7–4 over the Mighty Ducks of Anaheim, in relief of starting goaltender Evgeni Nabokov. He made his first start on April 8, again against Anaheim, and earned his second win.