After leaving junior high school, Winterburn went on to have tremendous accomplishments at Jamestown High School. He joined the baseball club as a freshman and as a sophomore won the Lake Shore League batting and pitching titles in 1953. He hit .500 right on the button and compiled a 3-0 mark as the Red Raiders won the championship.
In 1954, Winterburn sparked Coach Walt Colburn's club to a 15-1 ledger and the first Section 6 Class AA title since 1949 by beating Kenmore 7-2. The following year, Winterburn regained the Lake Shore League pitching title with a 4-0 and had two shutouts, including a 15-strikeout, 9-0 verdict over Dunkirk.
That same year, the Raiders captured another league crown with a 9-1 record and Winterburn batted .360 while dividing duties between the mound and the first base for a club which averaged nearly 11 runs per outing.
Beside baseball, Winterburn excelled in basketball and was named to the All-Western New York All-Star Team as a senior. Not very many Jamestown or Chautauqua County players have ever been bestowed with that honor.
The 6-6 Winterburn didn't attend college but definitely toured the country as he became a member of the bearded House of David basketball team from 1957-1960. The House of David was known as the "world's most colorful basketball club" and featured several former collegiate stars.
Winterburn averaged 23 points a game in performing against teams across the United States, Mexico and Canada when the House of David scheduled yearly over 200 games with the season ranging from April to October. He averaged around 150 contests per year.
Oddly enough, one of the local games that the House of David played was an 80-72 victory over the Jamestown YMCA, led by another 1993 Chautauqua Sports Hall of Fame inductee, Leo Corkery. Winterburn tossed in 32 points to be his team leader while high on the losing side was Corkery with 29 markers.
In the 1960s, Winterburn first set the Jamestown YMCA record with 42 points and later that year he topped that with 46, including an amazing 24-25 free throws in a 111-86 loss to Franklin, Pennsylvania.
From 1961-1964, he performed for Warren Beverage, which at that time was regarded the best in the area. He also played for Sluga's and Witch-Kitch Inn.
In the summer, baseball was the focus as he performed for Warren Beverage, which captured the Pennsylvania-Ohio titles in 1963. Then in 1964, Winterburn competed in the National Baseball Congress Tournament in Wichita, Kansas. Also there was a young pitcher and a future Hall-of-Famer named Tom Seaver, the star who made his mark with the New York Mets and the Cincinnati Reds.
Winterburn received a certificate as being one of the 16 all-star players from the Chautauqua County League to appear at the National Baseball Congress Tournament.
Besides playing baseball in the summer, Winterburn also got involved in softball as he began playing fast-pitch in the late 1950s and then went to modified in the early 1960s.
He has earned numerous "Most Valuable Player" trophies in his distinguished career while hurling several no-hitters in both baseball and softball. One of his no-hitters in softball was a 10-0 win for Frewsburg Hotel over Mickey Rats in the Social Modified League (later known as the Tim Brown League) in 1980. He has also pitched Heintz's Vending to several wins, including tournament competition.
Winterburn coached softball and basketball in the Church League plus he was a host parent with his wife Carol for several Babe Ruth World Series. For several years he worked the chains along with Kenny Martin, Bob Jursted and Bob Benson for the Jamestown High School football games and continued to play some softball and golf.