West Ham United’s U23s have been drawn alongside London rivals Tottenham Hotspur in this season’s Premier League International Cup Group F.
The Hammers will also face Portuguese side Benfica and Spanish outfit Villarreal in the prestigious tournament which contains some of Europe’s top academy sides.
As a member of this season’s Premier League 2 Division 1 having secured promotion via the play-offs last season, Terry Westley’s men were entered in the tournament and will gain vital experience facing a number of huge clubs.
After the draw, the boss said: "The whole games programme for that age-group this year is a real challenge and the International Cup is part of that. The decision on whether you send people on loan or if they stay with your group, that's a challenging decision now.
"In October, we have Chelsea, Manchester United and Manchester City as well as Bristol Rovers in the Checkatrade Trophy, then now you may throw Benfica into that.
"These teams will be real technical teams - but so are Man City and Chelsea and Tottenham at those age-groups. We're excited for the challenge but it's a massive one."
The London derby will be one of three against Spurs – also part of Division 1 – for the youngsters this campaign and comes just ten days after their opening meeting of the season, at their opponents' training ground on Monday 21 August.
West Ham’s second opponents – after facing their Tottenham at Stevenage’s Lamex Stadium on Thursday 31 August – are the 2015/16 winners of the competition, Villarreal.
Last season, Sunderland were the most successful English club, reaching the final before eventually losing out to Porto 5-0 at the Stadium of Light.
The Hammers will host The Yellow Submarine at Dagenham and Redbridge’s Chigwell Construction Stadium just six days after their first tie, on Wednesday 6 September.
The date of the fixture against Benfica is still to be confirmed.
For full details of all of West Ham United Premier League 2’s fixtures, click here.