Kendall was born in Milwaukee, Wisconsin, .[3][4][5][6] He attended Nicolet High School in Milwaukee.[7] In high school he played three sports.[8] In soccer, he made the All-State team as a senior.[8] In basketball, he was team MVP and team captain in 1982.[8] In golf, he finished second in the state as both a sophomore and a senior.[8]
The 1999 season was among his best on the PGA Tour. In addition to his second place finish at Hartford he finished T10 at the Players Championship. That season he recorded his highest ranking on the Official World Golf Ranking of #68.[9] Overall he recorded 13 top-25 finishes, made 24 cuts, and earned $962,642. He also earned $1,206,438 in 2004 with seven top-25 finishes.
He also has four Nationwide Tour victories.
Since 2014, Kendall has played on the PGA Tour Champions and has had three top-10 finishes.
In 2015, Kendall missed the cut for the Puerto Rico Open and the Barbasol Championship, scoring 78 in both events on the first round and ended up getting 9-over-par in both tournaments. He did however finish 2015 ranked 69th on the 2015 Champions Tour money list, and finished T10 at the 2015 Shaw Charity Classic.
Kendall is credited with introducing Chris DiMarco to the "claw" putting grip.[10][11]
Kendall finished his PGA Tour career with over $9.8 million in earnings.