[4][5] As a sophomore Bossert played the 1980–81 season for Sweet Home High School and helped oust Kenmore West in a 1981 NYSPHSAA Section VI Class A-1 semifinal.
[1] The leading votegetter on the All-NFL team, he scored 119 points in four NYSPHSAA Section VI playoff games, including an upset victory over his formerly unbeaten Sweet Home teammates,[1] in which he posted a 10–16 field goal and 9–10 free throw performance.
[6] On March 9, 1982, Bossert went 26–26 from the free throw line and totaled 44 points for Kenmore West in the NYSPHSAA Section VI Class A championship game loss to South Park High School.
[13] In the summer of 1982, Bossert was selected to the West New York Team for the Empire State Games scholastic (17 & under) boys' basketball competition, but did not see much action behind future Big East guards Aiken and Greg Monroe.
[12] In the 1983 NYSPHSAA Section VI Class A-1 championship game at the Buffalo Memorial Auditorium, Sweet Home overcame a game-high 32 points by Bossert to beat Kenmore West in double overtime.
[12] The Basketball Coaches Association of New York, celebrated their 25th anniversary in 2007 by naming regional 25-year teams for the 1983–2007 period based on high school performances.
[22] When Niagara defeated the #4-ranked and 5–0 1984–85 St. John's Redmen on December 15, 1984, in one of the biggest upsets in school history, Bossert played key minutes.
The game, which featured Redmen all-time greats Chris Mullin, Mark Jackson, Walter Berry and Bill Wennington and was hosted at the Niagara Falls Convention Center, has been dubbed "Miracle on Fourth Street".
[28] According to sports journalist Bob Lowe of the Tonawanda News it took Bossert, who had filled out to a size of 5 ft 9 in (1.75 m) and 160 pounds (72.6 kg) by the beginning of 1986, a couple of years of NCAA Division I play to adapt to defending bigger guards at that level.
Lowe also described Bossert as an adept ballhandler and asset on the offensive end of the floor who could be described as the "coach on the court", "traffic cop" or "quarterback".
[34] On February 5, 1987, he made a three-point shot with 8 or 9 seconds left to give Niagara a victory over the Reggie Lewis-led 1986–87 Northeastern Huskies.
In the opening round of the tournament, they defeated a Seton Hall team led by Mark Bryant and Ramón Ramos.
[38] They subsequently lost to a La Salle team with Lionel Simmons, Craig Conlin, Tim Legler, and Larry Koretz,[39] despite 16 points by Bossert.
[41] For the 1986–87 NCAA Division I men's basketball season the National Collegiate Athletic Association introduced the three-point shot.
[42] On January 7, 1987, Bossert became the first player to make at least 12 three point shots in a game for Niagara against Siena in an NCAA Division I America East contest.
[44] However, it was unsurpassed until December 21, 1989, when Dave Jamerson went 14-for-17 for the Ohio Bobcats of the Mid-American Conference against NCAA Division II's Charleston Golden Eagles.
[31] While some still recognized Bossert's as the holder of the single-game three point shots made record, another Western New York athlete set the National Junior College Athletic Association single-game three point shots made record, when Bill Perkins went 17–40 for Villa Maria College in a victory over Jamestown Community College-Olean on November 20, 1990.
[54] After his NCAA record-setting night, Bossert gave an opinion that the newly created three-point line distance should be 1 to 2 feet (0.30 to 0.61 m) further.
That summer, Bossert assumed varsity basketball coaching as well as scholastic business course instruction responsibilities at Norwood-Norfolk Central in Norfolk, New York.
[3] Darrin Bossert played for Niagara from 1989 to 1991 and is among the school's all-time leaders with a career 39.2% three point field goal percentage.