Tony Carr is hoping his Under-18s strike it third time lucky in the Midlands when they head to Coventry City on Saturday.
West Ham United's scholars have been beaten at both West Bromwich Albion (3-2) and Birmingham City (2-0) in the FA Premier Academy League already this season - in direct contrast to the sparkling home form that has seen them defeat Middlesbrough (5-1) and MK Dons (3-0) at Little Heath.
West Ham sit second in Group A, while the Sky Blues are third in Group B, having won two and drawn one of their four matches played so far. Coventry won 2-1 at Fulham last Saturday.
Having comfortably brushed aside MK Dons last weekend, the Academy Director has challenged his young squad to rise to the occasion at Coventry.
"Our two home games have been very good, but our two away games have ended in disappointing results. We're going back to the Midlands again - we've been to West Bromwich Albion, we've been to Birmingham and now we go to Coventry and obviously I'm looking to get something from the game.
"There are areas of the game that I feel we've not been good at - basically we lose possession of the ball more quickly than we win it back and we've been working very hard at that. Hopefully we can go to Coventry and put in a reasonable display and get a positive result.
"Their results have also been a bit mixed and similar to ours in that respect, but when you go to these places they are always tough games. At youth level, it's always competitive, but we'll take two teams up there and hopefully we'll have better news after this one than after the last two away games."
One of Carr's concerns in the youth team's opening matches has been their ability to adapt to the more physical nature of U18 football.
With many of the starting XI first-year scholars and just a handful of months past their 16th birthdays, the Hammers have come up against older, more experienced and more physically-developed opponents.
Having contested a number of pre-season friendly matches against senior men's sides, Carr is confident his youngsters will rise to the challenge.
"It is certainly true to say that the boys are a few months out of school and the game starts to become more competitive. Results mean a little bit more - they are not the be all and end all, but we're getting to the stage where you need to get a result as well as play well. Obviously, when you combine the two things together, that's what we're looking for.
"We are a very young squad this year, so hopefully we can get better as the year goes on and come of age, you might say."