One of the earliest results recorded in program history is a one-point overtime road loss to the University of Maryland Terrapins on January 25, 1913.

[1][2] With a recorded history spanning more than 110 years, the program is one of the oldest high school basketball teams in the United States.

Parker replaced Phipps as head coach in 1969, and guided the team to the MSA conference championship in his first season at the helm.

[13][14][15][4] The Black Knights have advanced to the MPSSAA state tournament semifinals eight times (1997, 1998, 1999, 2009, 2010, 2014, 2022, 2023), third most all-time among Baltimore City League teams.

[16][17] Wayne Cook took over as head boys basketball coach in 1989 and led City College to the school's final MSA victory in 1993.

Following a 10-10 finish in 1993-94, Daryl Wade replaced Cook as head boys basketball coach prior to the 1994-95 season.

1 ranking in the final Baltimore Sun basketball poll, Daniel was named All-Metro Coach of the Year in 2010.

[22] In 2011, City ended its season with a mark of 16–9 and ranked No 6. in the final Baltimore Sun boys basketball poll following a loss to Edmondson in the regional semifinals.

[24] At the start of the 2011–12 season, Daryl Wade rejoined the program for the second time as head boys basketball coach.

[25] In his first season back as head coach, Wade guided the team to a record of 21-6 and lost in the MPSSAA regional semifinals to eventual state champion Patterson.

18-ranked team in the United States in the final USA Today Super 25 and Student Sports Fab 50 national boys basketball polls.

[4][38][39] City College finished the season ranked among the top-20 nationally in the USA Today Super 25 boys basketball poll twice since 2010, and boasts 12 First Team All-Metro players since 2007.

Fair, who helped lead City College to a 25–4 record and the regional semifinals as a sophomore, was named 2013 ACC Preseason Player of the Year at Syracuse.

[43] Former forward Charles Tapper played basketball and football at City and was a First Team All-Big 12 Conference defensive end for the Oklahoma Sooners in 2013.

[44] Will Barton, a current member of the NBA's Toronto Raptors, was a shooting guard at City College before ultimately finishing his high school basketball career at Brewster Academy in New Hampshire.

Head coach Omarr Smith led the Knights to its second consecutive 3A state semifinal appearance and finished the season as the No.

2-ranked team in the Baltimore Sun final boys basketball poll behind nationally-ranked Mount Saint Joseph High School.

18 nationally in the final USA Today Super 25 and Student Sports Fab 50 boys basketball polls, the second highest ranking of any team in Maryland, Pennsylvania, Virginia, and Washington, D.C.[30][31] In 1967, City completed its second of two consecutive undefeated seasons under Coach Jerry Phipps.

City was coached by Jerry Phipps and led by Lee Dedmon, who became an All-Atlantic Coast Conference center at North Carolina.