England Women's preparations for this summer's World Cup suffered a blow as they were beaten 1-0 by Canada Women in a friendly at Manchester City's Academy Stadium.
England struggled to get going in the first half, and it took until the dying embers of the opening period for Stephanie Labbe to be tested in the Canada goal, as she denied Nikita Parris.
After the break, England did improve, but still could not create much in the way of clear-cut chances, with Toni Duggan wasting England's best opportunity after firing just wide.
With England pressing for a winner of their own, Christine Sinclair's 180th international goal won it for Canada in the 81st minute, as England suffered a disappointing defeat - just their third defeat since Phil Neville became coach.
England started well against a side ranked two places below them in Manchester, with Parris causing problems down the right flank, but each time the final pass was lacking.
Down the other end, veteran striker Sinclair had an effort from fully 25 yards, but it was never going to trouble Karen Bardsley in the home goal.
Parris remained England's best outlet, as she finally had that effort at goal after being picked out by a fine Jodie Taylor pass, but Labbe was down well to tip the strike around the post.
After the break, Janine Beckie forced a brilliant save out of Bardsley as the visitors pressed for an opener.
Duggan then almost got a sellout crowd off their feet but, after being picked out by Taylor in the penalty area, fired just wide on the hour mark.
It was clear one goal was going to win this cagey affair, and so it proved as Bardsley's brilliant save to tip Nichelle Prince's effort onto the crossbar was in vain, as the 35-year-old poacher Sinclair was on hand to snatch victory for Canada, inflicting a defeat on England which leaves Neville with much to ponder just two months ahead of the World Cup.
Player of the match - Nikita Parris
No other player caused anything like the problems that Parris did down the right flank with her direct running and pace. Her final ball was lacking more often than not, but she still created all the best openings for England, but just suffered from a shortage of support.
What's next
England travel to Swindon to take Spain in a friendly on Tuesday, while Canada host Nigeria on Wednesday.