The team's best result ever came in its first appearance in 1913 when it reached the World Group final, losing to the United States 0–3. Canada's best result in the Open Era was in 2013 when they reached the World Group semifinals, but were defeated 2–3 by Serbia.
Canada competed in its first Davis Cup in 1913. The team won its first tie, played in June at the Queen's Club, London over South Africa by a score of 4–1. The team consisted of just two players, Robert Powell and Bernard Schwengers. Canada then in July easily defeated Belgium in the semi-finals 4–0. In the playoff final however, played a week later, they lost all three matches to the Americans in straight sets. (The Americans went on to defeat Great Britain in the challenge round, to win the competition.)
Canada did not play a World Group tie from 1921 until 1991, when the team of Grant Connell, Glenn Michibata, Andrew Sznajder, and Martin Wostenholme, with team captain Pierre Lamarche, lost 1–4 away to Spain. The following year, again in the World Group first round, Canada came closer to advancing, going down 2–3 at home to Sweden despite taking a first-day 2–0 lead. The tie was highlighted by a surprise singles win of rookie Daniel Nestor over superstar and then world number one ranked Stefan Edberg. Nestor could not repeat the magic, however, losing in the deciding rubber match in 5 sets to Magnus Gustafsson.
In 2012, Canada played against France in the first round of the World Group, but lost 1–4. Pospisil lost the first match 1–6, 3–6, 3–6 to Jo-Wilfried Tsonga and Raonic won the next one against Julien Benneteau 6–2, 6–4, 7–5 to end day one at 1–1. Canada then lost the three next matches (the doubles 6–7(1–7), 6–7(2–7), 3–6 and the last match 4–6, 4–6) as Raonic had to withdraw for his second singles match against Tsonga following an injury on his left knee. He was replaced by Dancevic who lost 4–6, 4–6, 1–6. Canada secured its spot in the World Group in 2013, and for the second straight year, with a 4–1 victory over South Africa in the playoffs in September. Canada had only played two straight years in the World Group one other time in its history before that, in 1991–92.
In 2013, Canada upset the number one ranked tennis nation Spain 3–2 in the first round of the World Group, the first win ever for Canada at that stage in the Open Era. Raonic won the first match 6–7(5–7), 6–4, 6–4, 6–4 over Albert Ramos and Dancevic defeated then World No. 34 Marcel Granollers 6–1, 6–2, 6–2 to give Canada a 2–0 lead after the first day. Canada's doubles team of Nestor and Pospisil lost 6–4, 4–6, 7–6(7–4), 3–6, 2–6 to Marc López and Granollers, but Raonic secured the win for Canada in the final day with a 6–3, 6–4, 6–2 victory over Guillermo García-López. Dancevic lost the last match 5–7, 4–6 to Ramos. Canada then defeated in April Italy 3–1 in the quarterfinals to reach the second semifinal of its history, the first in the Open Era. Italy's Andreas Seppi won the first match 5–7, 4–6, 6–4, 6–3, 6–3 over Pospisil, but Raonic answered back with a 6–4, 7–6(7–4), 7–5 victory over Fabio Fognini. The Canadian doubles team of Nestor and Pospisil took the crucial doubles match in a marathon of almost four hours and a half, 6–3, 6–4, 3–6, 3–6, 15–13 over Daniele Bracciali and Fognini. Raonic gave Canada the win after defeating Seppi 6–4, 6–4, 3–6, 7–5 in the final day. Canada was eliminated 2–3 by Serbia in the semifinals in September. World No. 1 Novak Djokovic won the first match 6–2, 6–0, 6–4 over Pospisil and Raonic took the second 5–7, 6–3, 3–6, 6–3, 10–8 over Janko Tipsarević to end day one at 1–1. Canada had a 2–1 lead after the second day when the doubles team of Nestor and Pospisil defeated Nenad Zimonjić and Ilija Bozoljac 6–7(6–8), 6–4, 3–6, 7–6(7–5), 10–8. Raonic and Pospisil both lost their matches the final day, respectively 6–7(1–7), 2–6, 2–6 to Djokovic and 6–7(3–7), 2–6, 6–7(6–8) to Tipsarević. Canada will stay in the World Group in 2014 for a third straight year, a record.
In 2014, a very diminished Canadian team lost in the World Group first round to Japan 1–4 as both Raonic and Pospisil were injured and not able to play. Canada then had to play a playoff in September against Colombia to stay in the World Group next year. They won the tie 3–2 meaning that Canada will play in the World Group for the fourth straight year.
In 2015, Canada had their revenge over Japan with a 3–2 win in the first round of the World Group. Raonic defeated Tatsuma Ito in straight sets in the first match and Kei Nishikori won against Pospisil to end the first day in a 1–1 tie. The next day, Canada's doubles team of Nestor and Pospisil won a closely contested match over Go Soeda and Yasutaka Uchiyama to give a 2–1 lead to Canada. Nishikori defeated Raonic in five sets the last day but Pospisil secured the victory for Canada with a straight-set win over Soeda. Canada will next play its quarterfinal tie against Belgium in July on the road.