The City of Toronto doesn't own or maintain streetlights or their poles; streetlight outages/issue (also damaged or graffitied poles) can be reported to Toronto Hydro via their web form: https://www.torontohydro.com/sites/electricsystem/residential/customercare/pages/reportastreetlightout.aspx
I'll close this off (you can reopen if you disagree but I'm pretty sure I'm correct. :^) )