Ingram was born and raised in Richmond, Virginia, and grew up in a tight-knit family of four. He loved basketball from an early age, and by the time he turned 12, he was beating his older brother by seven years, Lucius, in one-on-one.
Ingram attended Highland Springs High School in Highland Springs, Virginia, where he led the basketball team to the Group AAA championship as a senior in 2002–03, the first title in school history. That year, he averaged 22.8 points and 9.5 rebounds per game, while shooting 49 percent from three-point range. He was subsequently named the Associated Press Group AAA Player of the Year for his division. He left Highland Springs as a two-time Capital District Player of the Year and First-Team All-Metro, and as a senior was a First-Team All-State and First-Team All-Central Region pick.
As a freshman at American University in 2003–04, Ingram started in all 31 games and led the team with 13.6 points per game, which ranked fifth best in the league. He was subsequently named Patriot League Freshman of the Year, becoming the first American player to win the award. He had 16 points, five rebounds, two assists and two steals against Maryland on November 22, 2003 in his first collegiate game. On January 14, 2004, he made eight shots from behind the arc in a 27-point effort against Navy, which ties the second best single game three-point total in AU history. In addition, his 15 three-point attempts against Navy is tied for the highest single game attempt total for an Eagle. He went on to score a career-high 30 points on 10-of-19 shooting against Lafayette on February 28.
As a sophomore in 2004–05, Ingram played in 28 games with 27 starts and was named first-team All-Patriot League. He finished the season as the PL's second-leading scoring, just half a point out of the lead, with 15.3 points per game. After being named the PL Preseason Player of the Year, Ingram opened the season with 38 points against VCU. He registered six 20+ point performances in 28 games, including two 30+ point performances. He was named Patriot League Player of the Week twice during February 2005, and at the season's end, he was named National Association of Basketball Coaches All-District 4 Second Team.
As a junior in 2005–06, Ingram played and started in all 29 games. He led team in scoring for the third consecutive season, averaging 12.0 points per game. He scored in double-digits in 19 of 29 games, starting the season with a 24-point effort against Washington on November 19. He notched his 1,000th career point, while amassing a season-high 10 rebounds, against the Saint Francis Red Flash on January 2. At the season's end, he earned second-team All-Patriot League honors.
As a senior in 2006–07, Ingram ranked fifth in the Patriot League in scoring (15.2 ppg), second in three-point field goal percentage (.424) and second in three-point field goals made per game (2.6). He scored 20 or more points eight times, including a season-high 25 points against Lafayette. He subsequently earned first-team All-Patriot League honors for the second time in three years.
Ingram finished his collegiate career as American's fifth all-time leading scorer with 1,655 points, as he led team in scoring all four years.
On November 1, 2007, Ingram was selected by the Utah Flash in the seventh round of the 2007 NBA Development League Draft. He spent four years with the Flash, and in that time, became the franchise's all-time leading scorer with 2,098 points. He also ranks second in rebounds (608), fourth in assists (336), and third in steals (184).
Ingram had a career-best year in 2009–10, as he won the Jason Collier Sportsmanship Award and participated in 2010 NBA D-League All-Star festivities in Dallas, where he took home the Three-Point Shooting Competition Championship. Ingram made noteworthy contributions in game as well, starting 49 of the team's 50 games, and averaging 12.9 points, 3.9 rebounds, 2.1 assists and 1.5 steals in 34.0 minutes. He scored in double figures 36 times, including a season-high 24 points in a 104–99 road victory over the Bakersfield Jam on December 5, 2009.
Following the 2010–11 season, the Flash suspended operations and left Ingram without a team for the 2011–12 season.
On March 22, 2012, Ingram was acquired by the Los Angeles D-Fenders. He spent the rest of the 2011–12 season with the D-Fenders, playing in six regular season games and seven playoff games.
After sitting out the entire 2012–13 season, Ingram returned to the D-Fenders for the 2013–14 season. In 45 games (11 starts) with the D-Fenders in 2013–14, Ingram posted averages of 9.1 points, 3.2 rebounds and 1.7 assists, while shooting .447 from three-point range and helping the D-Fenders to a West Division Championship.
Ingram did not return to the D-Fenders for the start of 2014–15 season. He missed the first two months of the season before joining the team on January 12, 2015.
Ingram spent only his second full season with the D-Fenders in 2015–16. In February 2016, he became the D-League's all-time leader in three-pointers made and won his second three-point contest title. He took the crown by making 39-of-50 shots over two rounds – an all-time record across the NBA and D-League.
On October 18, 2016, Ingram signed with the Perth Wildcats for the rest of the 2016–17 NBL season, marking his first stint overseas. However, he managed just two games for the Wildcats before requesting his release from the club a week after landing in Perth, citing mental health reasons for the sudden decision.