Guidugli played at Highlands High School in Fort Thomas, Kentucky. He led Highlands to two state championships in 1999 and 2000 and he also was a backup when Highlands won state in 1998. He still holds many Kentucky records for quarterbacks. He also excelled on the basketball court. He led his basketball team to the Kentucky sweet sixteen his senior season with a buzzer beating shot against Covington Holmes.
“Oh, mentally, Kenny’s on it now,” quarterbacks coach Gino Guidugli said after a recent practice ... Guidugli smiled at the memory ... That was supposed to be this,’ “ Guidugli said, recounting his response.