Canada 238 for 8 (Wijeyeratne 63, Dutta 56, Perchard 3-38) beat Jersey 207 (Lawrenson 66, Greenwood 59, Gordon 3-30, Zafar 3-51) by 31 runs
Windhoek: Half-centuries by Josh Lawrenson and Nick Greenwood were not enough as Jersey lost to Canada by 31 runs at the ICC World Cup qualifier play-off.
The island side restricted Canada to 238-8 in Windhoek, their first match to carry one-day international status.
Captain Charles Perchard took 3-38 and opener Greenwood then launched the run-chase with 59 off 70 balls.
Lawrenson top-scored with 66 off 101 but fell at the start of the 40th over and they were bowled out for 207.
Jersey's next game is on Thursday against hosts Namibia, who lost to the United States by 80 runs in their opening fixture.
Papua New Guinea and the United Arab Emirates are the other teams involved - the UAE won by 21 runs in their match on Monday - and the top two will progress to the final stage of qualifying in India in October.
Having won the toss, Jersey justified Perchard's decision to field first by reducing the Canadians to 52-4.
But a sixth-wicket stand of 70 between Srimantha Wijeyaratne (63) and Nikhil Dutta (56) helped them push on beyond 200 and Ravindepal Singh added a final flourish with an unbeaten 21 off 18 balls.
Harrison Carlyon (18) was caught in the ninth over of Jersey's reply, but Greenwood hit two sixes - the second carrying him to 50 off 62 balls - and five fours in his aggressive knock.
His 81-run partnership with Lawrenson came to an end when he was caught behind off Pargat Singh from the final ball of the 24th over.
Jonty Jenner batted brightly for 20 before being bowled by left-arm spinner Saad bin Zafar (3-51) but the key wicket was that off Lawrenson, stumped off Dutta at the start of the 40th.
Jersey had the rate down below a run per ball at one stage but the task of seeing them home was beyond the tail as the last four wickets fell for 12 runs in the space of overs - with Perchard last to go, caught and bowled off Jeremy Gordon (3-30).