Joe Cole's debut for Liverpool ended in defeat as the Reds went down 1-0 to Borussia Monchengladbach.
Roy Hodgson fielded a strong side including England's World Cup captain Steven Gerrard as well as Jamie Carragher and Glen Johnson while Fabio Aurelio was named on the bench after re-signing for the club.
Monchengladbach had arranged the match as part of their 110th anniversary celebrations at Borussia Park and the hosts made an early breakthrough through Karim Matmour in the eighth minute. The Algerian took advantage of some poor play by Daniel Ayala inside the area and the defender was duly punished as Matmour produced a powerful finish.
Matmour was proving a real irritant for the Anfield club and came close to doubling his side's lead with Liverpool having to wait until the 56th minute for their first real chance when Cole's low drive was parried, with the former Chelsea player withdrawn nine minutes later. The hosts continued to threaten and, although David Amoo headed narrowly wide, Monchengladbach fully deserved their victory.
A poor opening goal handed Eintracht Frankfurt a head start as Premier League champions Chelsea went down 2-1 in Germany.
With Patrick Ochs bearing down on goal, John Terry sent a misjudged backpass to Hilario who tried to beat the 26-year-old but instead allowed him to nip in and dispossess the Portuguese goalkeeper at the edge of the area. The German then traded passes with a team-mate before lobbing the ball into the net midway through the first half.
Chelsea drew level after 65 minutes when Frank Lampard burst through but the hosts scored the winning goal through Halil Altintop's penalty with seven minutes remaining, awarded for a shirt pull by Branislav Ivanovic.
There was better news for Arsenal as they won the Emirates Cup after a 3-2 victory over Celtic.
Theo Walcott took just three minutes to open up the Celtic defence as Carlos Vela swept the Gunners into the lead, before Bacary Sagna and Samir Nasri put the Gunners three up. Jack Wilshere - starting his second game of the weekend in central midfield - produced an all-action display which was almost capped by a goal when his stunning first-half volley smashed against the crossbar, but he gave Celtic a chance to get back into the game after hauling down Marc-Antoine Fortune to concede a needless penalty in the second half.
Georgios Samaras blazed it over the bar, but four minutes later Daryl Murphy netted and Ki Sung-Yueng gave the hosts a nervy last few moments when he added another on the break.
Aston Villa were hammered 4-1 by Benfica in the decider of the friendly Guadiana Cup tournament.
Goals from David Luiz, Javier Saviola and Oscar Cardozo saw Villa fall 3-0 down before the interval.
Saviola added a second five minutes after the restart, before substitute John Carew finally netted in the 68th minute for Villa, with a fine, though ultimately meaningless, goal.
A late goal by Matt Lowton saw Sheffield United claim a 1-0 win over South American champions Estudiantes at Bramall Lane. Lowton guided the ball home from eight yards with five minutes remaining as the npower Championship side overcame the 2009 Copa Libertadores winners.
A goal eight minutes from time by Ian Harte gave Carlisle victory over Hibernian in a low-key game at Brunton Park. Harte headed home a James Berrett corner after losing his marker to earn a deserved win for the League One side, who also came close through Craig Curran.
Hibs had a goal disallowed for an apparent offside in the first half but they produced little in attack after the break bar an attempt by Anthony Stokes which goalkeeper Adam Collin saved with his leg.
A late goal by Liam Davis earned Northampton a 2-2 draw with a Birmingham XI at Sixfields. The Premier League side fielded a strong line-up including James McFadden, Cameron Jerome and Lee Bowyer.
However, it was the Cobblers who went ahead when Billy McKay held off Liam Ridgewell to poke the ball past keeper Maik Taylor. Blues levelled five minutes after half-time through Jerome before McFadden put Alex McLeish's side ahead with a little over 20 minutes remaining. Davis, though, had the last word, scoring an equaliser with five minutes left.
Chester had an emphatic win as they beat a Wigan XI 4-0 at the Deva Stadium.