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Canada's James Pritchard scored on a late penalty kick in Canada’s 21-20 loss to Romania on Nov. 16, 2013 in Bucharest. In this file photo Pritchard scores his team's opening try against the U.S.A. during during first half Rugby World Cup Qualifying action in Toronto on Saturday August 24, 2013.CHRIS YOUNG/The Canadian Press

The second-half battle of the boot looked to be swinging Canada's way with 15 minutes remaining against Scotland on Saturday.

Having already knocked three penalties over to that point, Canada's all-time leading points scorer, James Pritchard, stepped up looking to put Canada back in the lead from what looked a relatively simple position 25 metres from goal.

However, his aim was awry and he clanged the ball against the upright, allowing Scotland to clear to safety.

Though he would atone for that miss five minutes later, those missed three points proved decisive in a 19-17 loss to the eight-ranked Scots, who registered a first-ever victory on Canadian soil in the process.

If that was one turning point, the controversial dismissal of Canadian flanker Jebb Sinclair with five minutes remaining was another. With Canada desperately chasing the one score that would take it into the lead, the London Irish loose forward caught replacement Scotland fly half Ruaridh Jackson with an innocuous elbow while his opponent was making a tackle. After conferring with the video official, referee Mike Fraser brandished a red card in the game's biggest talking point.

"It changed momentum," said Scotland head coach Vern Cotter, who celebrated his second game in charge with a second straight victory. "They were attacking at that stage and that probably turned the game before the end.

"We know always in these games little things make a difference and it was a little thing that turned out to be a big thing and had a reasonably big consequence on the result."

Despite the end result – another sickening game that got away following one from last week's capitulation against Japan - Canada can take heart that it was right in this contest against a Tier 1 rugby nation. Fifteen months out from the World Cup, head coach Kieran Crowley's side can feel confident that with a little more discipline and a little better finishing ability it will be a team that others sit up and take notice of in England next September.

"I'm sure that call [on Sinclair] is what is going to be talked about a lot this week but in all honesty I don't think it should have come down to that," said Canadian captain Tyler Ardron. "I think we should have closed it out before that so it shouldn't have made a difference. We're going to be really disappointed and we should, we can't lose games like that any more."

The Canadians' mood at the end of the game was a far cry from the attacking verve they showed from the opening kickoff.

Despite falling behind to a penalty from Scotland captain Greig Laidlaw in the third minute, the early going offered solid promise for the home side, which the Scotland coach attributed to a carry-over of the anger from last week's defeat against Japan.

Crowley's side was certainly on the front foot during the first period of the game, pinning the more acclaimed visitors inside their five-minute line, and minutes after falling behind, it appeared that scrum half Phil Mack had put Canada in front by touching down, but after a quick consultation with the TV match official, the referee pulled it back for a knock-on by Jeff Hassler.

The home crowd of 17,888, already enjoying a wonderfully temperate afternoon in the Toronto sunshine, was rewarded for its partisan support just after the 20-minute mark. Already back in the game courtesy of a James Pritchard penalty convert, things got even better thanks to a break from Ciaran Hearn, who sidestepped Scottish hooker Scott Lawson and bore down menacingly on the try line.

Though his charge was ultimately stopped by Laidlaw and Scottish fullback Stuart Hogg, he had the presence of mind to find teammate Hassler, who rolled across the line despite the close attention of Scottish counterpart Tim Visser, although the celebrations were dimmed by Pritchard's wayward conversion attempt.

Having endured the humid Houston heat in a 24-6 win over the United States last Saturday, Scotland was not about to crumble in far more palatable conditions at the habitual home of Toronto FC. Barely five minutes after Canada's try, Scotland were back at the races inside the Canada five-metre line, and when a goalline maul was held up, the ball was spun out to prop Grant Gilchrist, who touched down close enough to the posts to permit Laidlaw to add the convert.

The home side should have been back in front by the interval, but was let down by its red-zone offence, and that lack of finishing power allowed Scotland to escape unscathed, although it did lose flanker Alasdair Strokosch to injury. Following a 10-minute stoppage while the stretcher came on, Strokosch was replaced by Blair Cowan, and a further penalty by Laidlaw completed the scoring in the first half and allowed Scotland a 13-8 lead at the interval.

Pritchard's three penalties in the second half kept Canada in the running, but two from Laidlaw – including the decisive marker with eight minutes remaining - and a booming effort from Hogg from round about the halfway line put the icing on the cake for the visitors, who now head to far harder challenges in Argentina and South Africa. Canada meanwhile, prepares for the United States next week in Sacramento, always with one eye on next year's World Cup.

"Our program is slowly getting better and better and I think we're at the point where we can start taking a win from these top-tier teams," Hassler admitted. "These are the ones we need to push over in the last minutes and as it gets closer to the World Cup I think we will be someone to be reckoned with."

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