Upshaw attended Highland Park Junior High School and began to play organized basketball in Grade 8. He also played for the Africville Lakers in the Bantam (Under 14) and Midget (Under 16) boy's divisions in the local Metro Basketball Association.
Upshaw attended St. Patrick's High School in Halifax. He spent three years as a point guard for the St. Patrick's High School Fighting Irish, winning three consecutive provincial championships.[1]
Upshaw finished his high school athletic career by leading the St. Pat's Fighting Irish to a third consecutive provincial title. He scored 37 points to edge the Truro Cobequid Educational Centre Cougars. He was named the Halifax Metro League MVP for the 2004–05 season.[4]
He was also a two-time 100-meter sprint champion and a football wide receiver in high school.
He played collegiate basketball as a 5'11" guard for the St. Francis Xavier Men's Basketball team under head coach Steve Konchalski from 2006 to 2011.
2006-07 season
In his debut season with the St. FX X-Men, he scored 213 points in total and he led the team in steals with 33 over 18 games. He was named the St. FX Men's Basketball Rookie of the Year. Upshaw was also honored as the AUS Rookie of the Year for the 2006–2007 season. He was selected for the AUS All-Rookie Team and the CIS All-Rookie Team.[citation needed]
2007-08 season
In the 2007–08 season, he finished with 278 points over 20 games and ranked second in team scoring with a 13.9 points per game average. He led the X-Men in steals with 43 (2.15 per game).[5]
2008-09 season
As a third-year point guard for the St. FX X-Men, he scored 362 points, averaging 19.1 points per game for the season. Upshaw led the St. FX men's basketball team in assists (4.0 per game), free-throw percentage (81.7), and three-point FG percentage (47.9). His three-point percentage ranked him second in AUS.[6] He set a St. FX University record with nine three-pointers in a 38-point game against the Cape Breton Capers.[7] He was awarded the St. FX Men's Basketball Team MVP and earned his first Atlantic University Sport Most Valuable Player in the 2008–2009 season.
In the summer, Upshaw was chosen, among 11 other collegiate athletes from both the CIS and NCAA, to represent the 2009 Canadian Men's Development National Team at the 2009 Summer Universiade held in Belgrade, Serbia from July 1 to 12, 2009.[8]
2009-10 season
In the 2009–10 season, Upshaw appeared in all 20 regular season games for the X-Men. He finished third in league scoring with a 19.5 points per game average. He also led the conference in assists (6.0 per game), ranked fourth in AUS for steals (2.3 per game) and was seventh in free-throw percentage (81.4). He was awarded the team MVP and earned his second consecutive AUS MVP award.[9] He was also named a CIS first team All-Canadian for the second consecutive year which featured the MVPs of the nation's five conferences.[6]
2010-11 season
During his final season with the St. FX Men's Basketball team, he averaged 18.1 points per game, 4.8 assists per game, and 3.1 rebounds per game on 47 percent shooting. Upshaw was named the team MVP and an AUS First-Team All-Star.[10]
On November 3, 2011, Upshaw suffered a broken elbow when attempting a layup during the Rainmen's season opener against the London Lightning at the John Labatt Centre.[12] In January 2012, Upshaw was removed from the injured reserve list, allowing him to participate in a regular-season game for the Halifax Rainmen against the Oshawa Power at the Metro Centre.[13]
Following the 2012 NBL Canada draft in August of that year, the Rainmen disclosed a trade in which Tyrone Levett and Christian Upshaw were transferred to the Moncton Miracles in exchange for the Moncton Miracles' first-round draft pick, Anthony Johnson.
Upshaw was signed to play the 2014–15 ABA season with the Calgary Crush. He was later released from the Calgary Crush in 2014. He decided to stay in Calgary after stepping away from pro basketball.[citation needed]
