|High School:||Deerfield Academy|
2016-17: No. 1 nationally ranked Khalifa became the first-ever Columbia squash player to win a national championship, defeating Rochester's Mario Yanez (11-1, 11-6, 11-5) in the final round of CSA Individual National Championships Pool Trophy (A Division)...Earned first team All-America honors for the third straight season...Ivy League Player of the year with a 6-1 Ivy record for the second straight season...Put together a 15-1 record in the No.1 position...Started the season with nine straight victories in the top position...Went undefeated at CSA Team Nationals with wins over Drexel's Omar El Atmas (11-4, 11-4, 11-5), Harvard's Saadeldin Aboudaish (8-11, 11-9, 11-4, 7-11, 11-0), and St. Lawrence's Mohamed El Gawarhy (11-9, 2-11, 11-5, 11-5)... Was a team captain in his junior season... William V. Campbell Performer of the Year.
2015-16: Behind a 7-0 Ancient Eight record at the No.1 position, Khalifa became the second player in program history to earn Ivy League Player of the Year honors...A 9-0 regular season record and a CSA National Championships Pool Tropy (A Division) apperance led to a second consecutive first team All-America selection.
2014-15: Put together a 15-1 regular season record mainly at the #2 position. He also picked a pair of victories at the top position against Harvard's Madhav Dhingea and Brown's Jack Blasberg....Capped the season competing in the title match of the CSA National Championship posting a runner-up finish. On his way to the title match, Khalfia was stellar in his national championship debut. The first-year won four straight matches in two days in straight sets. On day one, Khalifa began with an opening round 3-0 victory over St. Lawrence's Ibrahim Khan (11-3, 11-7, 11-3) and followed with a defeat of Rick Penders (15-13, 11-1, 11-7), a member of reigning national team champion Trinity. He returned in day two to take down Princeton's Samuel Kang in the quarterfinals (11-3, 11-3, 11-7) and went on to blank Harvard's David Ryan in the semi-finals (11-7, 11-8, 11-8)....With a remarkable 20-2 overall record this season, Khalifa capped his 2015 campaign with a first team All-America honors....Became the second player in program history to earn Ivy League Rookie of the Year and first team All-Ivy League honors.
At Deerfield Academy: He is a two-time letterwinner of squash at Deerfield Academy. At Deerfield, helped capture back-toback New Englang Championships in 2013 and 2014. He remained undefeated at the top position from 2012-2014. Khalifa is an experienced winner having won the Dutch Junior Open (2009, 2010, 2011), the German Pioneer Cup (2008, 2010, 2011), the British and French Junior Open (2008) and a US Open finalist in 2013.
Personal: Osama Khalifa's brother Amr Khalifa (St. Lawrence 14') also won the squash national championship in 2013.