For the Woodlawn Cardinals and Coach Tom Copple, the 1986-87 season was one of the best in the school's history. The Cardinals captured the first Class A Regional Title in boys basketball in the school's history by defeating Waltonville 41-23 in the Class A Waltonville Regional. The team ended a spectacular season at 24-4 after a 51-38 loss to Okawville in the first round of the Class A Sparta Sectional.

The Cardinals won the 33rd annual Conrad Allen Holiday Tourney held at Wayne City in December by defeating Waltonville 65-49. John Dale, Shane Witzel, Jason Petersen and Scott Teems were named to the Conrad Allen all-tournament team.

In late January, the Cardinals defeated Mascoutah (a Class AA school) 42-34 and Breese Mater Kei (a much larger school) 65-56 to capture the Nashville, Invitational title. Shane Witzel and Jason Petersen were named to the Nashville Invitational all-tournament team.

The Cardinals won the Mid-South Conference title for the fourth straight year with a conference record of 9-1. Woodlawn has won the Mid-South Conference all four years since it began in 1984 and they also won the Quad-County Conference back in 1983. Shane Witzel, John Dale and Jason Petersen were selected to the all-Conference team.

Individual honors for the season included Scott Teems' selection to the Class A squad of the Southwesteren Illinois High School All-Star game played at Belleville Area College on May 3, 1987. Also, John Dale was named to the Southern Illinois Coaches Association All-Star team. The 1986-87 Season ranks among the finest in Cardinal history.