First: 31st May 1998 - London-Heathrow (LHR) to Toronto (YYZ) - Canadian Airlines - 5 weeks training for 1st day at new job (which I'm still doing after 22.5 years).
Last: 8th March 2020 - Fort Lauderdale (FLL) to Toronto (YYZ) - WestJet - Long weekend to catch up with a good friend and his family.