| 1785 | First confirmed reference to cricket in Canada as matches are played on Île Sainte-Hélène in Quebec. |
| 1827 | Toronto Cricket Club formed, now the Toronto Cricket, Skating and Curling Club, the premier club in Canada. |
| 1836 | First annual match between the Toronto Cricket Club and Upper Canada College is won by the college team. |
| 1844 | First international in any sport takes place as Canada take on the USA at cricket in New York, winning by 23 runs. |
| 1845 | First Canada v USA match in Canada takes place in Montreal. Canada win by 61 runs. |
| 1853 | Canada lose to the USA for the first time in Harlem. |
| 1859 | George Parr's XI tour Canada and the USA for the first international cricket tour. They beat 22 of Lower Canada by 8 wickets and a combined 22 of Canada/USA by an innings. |
| 1880 | Gentlemen of Canada tour the UK, including a match a Lord's against the MCC. They win 4 matches, lose 5 and draw 8. Low point of tour is when captain Thomas Jordan is revealed to be a pseudonym for Thomas Dale, a deserter from the British army, and he is arrested during the match against Leicestershire. |
| 1887 | Gentlemen of Canada tour UK again, losing two match series against the Gentlemen of Ireland and the Gentlemen of Scotland both 1-0, and win two matches out of 15 in England. |
| 1892 | Gentlemen of Ireland tour North America, drawing against the Gentlemen of Canada in Toronto. |
| 1893 | Australia tour North America, beating Canada by an innings. |
| 1913 | A combined Canada/USA team takes on Australia in two first-class matches, losing them both. The match in Toronto is the first first-class match in Canada. |
| 1951 | Canada play the MCC in a first-class match at the Toronto CSCC, losing by 151 runs. |
| 1954 | Canada tour England, playing first-class matches against Essex, Warwickshire, Pakistan and Yorkshire. |
| 1973 | Ivan Anderson scores a then Irish record innings of 198 not out when playing for Ireland against Canada at the Toronto CSCC. |
| 1974 | Canada tour England, playing mainly county second XI's. |
| 1979 | Canada finish as runners-up to Sri Lanka in the first ICC Trophy. Canada play their first ODIs as part of the World Cup, losing to Pakistan, England and Australia. |
| 1982 | Canada finish third in their first round group at the ICC Trophy. |
| 1986 | Canada finish fourth in their first round group at the ICC Trophy. |
| 1990 | Canada finish equal seventh in the ICC Trophy. |
| 1994 | Canada finish equal fifth in the ICC Trophy. |
| 1996 | Canada take part in West Indian domestic one-day cricket for the first time, losing all four of their completed matches. |
| 1997 | Canada finish seventh in the ICC Trophy. Canada reach the quarter finals of the Red Stripe Bowl. |
| 1998 | Canada play in the first Commonwealth Games cricket tournament, losing heavily to Australia, India and Antigua. |
| 1999 | Canada play in Red Stripe Bowl, but have two matches abandoned. They lose the only game to be played. |
| 2000 | Canada host and win the first Americas Championship. Canada win their first match in the Red Stripe Bowl against the USA. |
| 2001 | Canada tour Sri Lanka, winning three matches. Canada host the ICC Trophy and qualify for the World Cup after beating Scotland in the third place play-off. |
| 2002 | Canada Under-19s play in their first World Cup and tie against Bangladesh. Canada are runners-up to the USA in the Americas Championship in Argentina. Canada finish fifth in the ICC 6 Nations Challenge. West Indies A tour Canada. Canada win the one-day series 2-1 and draw the two-day match. Canada play in the Red Stripe Bowl and beat Antigua and the Rest of the Windward Islands. |
| 2003 | Canada's second World Cup is a series of highs and lows. They beat Bangladesh for their first win against a Test playing nation, John Davison scores the fastest World Cup century against the West Indies, but they are bowled out for the lowest World Cup total of 36 against Sri Lanka. Canada's last appearance in the Red Strip Bowl sees them lose all four of their matches. |
| 2004 | Canada Under-19s lose all six matches in the Under-19 World Cup. A weakened Canadian side loses all five matches at the ICC 6 Nations Challenge. Canada's first first-class match in 50 years sees John Davison take 17 wickets against the USA in Florida, the best first-class bowling figures since Jim Laker's 19 against Australia. Canada win the Americas Championship in Bermuda and qualify for the 2005 ICC Trophy. Canada lose to Scotland in the final of the first Intercontinental Cup. |
| 2005 | Canada finish third in the ICC Trophy and qualify for the 2007 World Cup. |
| 2006 | Canada play their first ODIs outside the World Cup against Zimbabwe and Bermuda in Trinidad. Kenya tour Canada, with Canada winning the Intercontinental Cup game, whilst Canada's first ODIs at home end in two defeats. Bermuda tour Canada, with the same results as the Kenya tour. Canada finish third in the Americas Championship after an upset loss to the Cayman Islands. Canada women play their first matches, losing a three match series to Bermuda. Canada are runners-up to the Netherlands in a ODI tri-series in South Africa. Ryan ten Doeschate scores a tournament record 259 not out against Canada in the Intercontinental Cup. |
| 2007 | Canada are forced to forfiet a game against Kenya when they are unable to field a team due to illness. Canada finish fourth in Division One of the World Cricket League. Canada's third World Cup sees them lose to England, Kenya and New Zealand. Canada lose their second Intercontinental Cup final, this time to Ireland. Canada win the first women's Americas Championship. Canada end the year with a poor tour of Africa featuring a severely weakend side. They lose Intercontinental Cup games to Kenya and Namibia, also losing two ODIs to Kenya. |