After graduation, Annarella served in the U.S. Navy during World War II. He then went to Ithaca College where he was a goalie on the lacrosse team for two years and center on the football team, also for two seasons. He graduated in 1950 with a bachelor's of science degree in physical education and in 1952 with a master's of science degree in physical education.Annarella began teaching in 1953 at Sherwood Central School in Aurora, New York, before moving on to Cassadaga Valley in September of 1954 as a physical education and health instructor. He remained there until his death in an auto accident in 1976.
He began 11-man football at Cassadaga Valley in 1954 and racked up a 103-65-7 record with 15 winning campaigns. In 1958 Cassadaga Valley was co-champion in the Valley Conference and sole champion in 1965, 1966 and 1967. During the period from 1965-1968, the Cougars were 21-2-1, including the school's only unbeaten 8-0 club in 1966 and 21-0-1 streak for one of the longest in Chautauqua County history.
Annarella joined the rare 100-win club with a 27-16 victory over Silver Creek on October 2, 1976.
In addition to starting 11-man football, Annarella started the wrestling program in 1955 and remained the coach until 1964 with nine Section 6 Class B Titles. He also started girls basketball in 1973 and continued to coach that team through 1976. He also started girls volleyball in 1972 and coached it through 1976.
Annarella had Section 6 championship squads in boys volleyball in 1956-1957, 1957-1958, 1958-1959 and 1964-1965. He coached it until 1968 and then took over again from 1971-1975.
Baseball was also a sport he coached from 1956-1962.
In the 1950s, Annarella helped form the Wrestling Officials Association and established the Sinclairville area summer recreation program in the mid-1950s. He also umpired baseball games for several campaigns in the Sinclairville-Cassadaga area.
Annarella was inducted into the New Castle Hall of Fame in April 1990 and each year the Annarella Award is given to the Cassadaga Valley football player who best exemplifies his spirit and dedication. There is a memorial trophy case named in his honor at the school and the football field was named in his honor in 1977.
The Chautauqua County area was shocked when Annarella, then 52, lost his life in an automobile crash when driving to a wrestling meet he was to officiate.