After missing the season-opening trip to Florida to play with the Canadian national team, she started all 14 games the rest of the season.

As a junior in 2006, Matheson co-captained the squad and led the Tigers with eight goals and five assists for 21 points despite missing five games to train with the Canadian national team.

After returning from the tournament, she earned a point in seven straight games of the 10 played and broke Princeton's single-game and career assist records with a four-assist performance against Rutgers.

[2] Diana Matheson played the second half of the 2008 season in Oslo, Norway, with Team Strømmen, becoming a runner-up in the Toppserien league and also in the annual Cup competition.

[4] In early 2013, it was announced that Matheson would be joining the Washington Spirit as part of the NWSL Player Allocation, a team in the newly founded National Women's Soccer League.

[9] After joining the team late in 2015 due to injury and participating in the 2015 FIFA Women's World Cup, Matheson scored three goals and had two assists in just nine games.

[11] Matheson tore her ACL while training with the Canadian National team in February and she would miss the entire 2017 season.

[14] As a regular player for Canada, Matheson is remarkable for possessing the speed and skill to hold her place in an international team that is known for its physical approach to the game, despite having a height of only 5 ft 0+1⁄4 in (1.53 m).

[16] At the 2011 Pan American Games, Matheson helped Canada win the gold medal against the defending champions Brazil.

[19] After Canada defeated the host team Great Britain in the quarterfinals, they suffered a last minute loss in extra time to the United States in the semifinals.

[27] In May 2019, Canada Soccer announced that Matheson had been ruled out of the 2019 World Cup due to a foot injury that would require surgery.

[29] In December 2022, Diana Matheson and business partner Thomas Gilbert, announced plans to launch a professional women's soccer league in Canada.

[30] The organisation, Project 8, outlined its vision to launch a professional league in 2025 "founded on the principles of inclusion, community, and identity."