I invest in a share matching program with my company. They pay a dividend that gets reinvested automatically, do I have to claim this?

Hello,

Yes, you will need to report it as investment income , the company's trading platform should provide a tax slip outlining dividends paid (and reinvested).  Hope this helps!

https://www.canada.ca/en/revenue-agency/services/tax/individuals/topics/about-your-tax-return/tax-return/completing-a-tax-return/personal-income/line-12100-interest-other-investment-income.html