An own goal in the 90th-minute on Wednesday cost Liverpool a 1-0 loss to AS Roma but an early spill left striker Fabio Borini with a much more worrisome right shoulder injury. (Manchester United thrash LA Galaxy 7-0 in Van Gaal's debut)
The 23-year-old Italian striker, a former Roma standout before coming to Liverpool, fell on an early tackle and came up holding his shoulder.
Liverpool said during the match that Borini's shoulder was not dislocated but further examination was needed in a tough setback during the opening minutes of the English Premier League side's pre-season US tour.
The only goal of the match came in the dying seconds of regular time when Roma's Marco Borriello bent his right leg and redirected a corner kick off Danish Liverpool defender Daniel Agger and into the net.
Borriello, a 32-year-old Italian striker, has been on loan to Juventus, Genoa and West Ham United over the past three seasons.
In other pre-season friendlies involving English clubs on Wednesday in North America, Tottenham edged host Toronto 3-2 while Aston Villa was at Dallas, Manchester City was at Kansas City and Manchester United was playing the Los Angeles Galaxy at the Rose Bowl.
Liverpool's Steven Gerrard played his first match since announcing Monday he was retiring from international play for England after serving as English captain at the World Cup last month.
Roma has signed England's Ashley Cole, who said he had US offers but "I'm not ready to relax on a beach yet."
Liverpool, who inserted teen Adam Phillips in the final minutes and saw him receive a yellow card for a rough tackle, played for the second time in three years at Fenway Park, the iconic 102-year-old stadium that serves as home to baseball's Boston Red Sox.
John Henry, the American who owns the Red Sox and Liverpool, watched his football club walk onto the pitch to "You'll Never Walk Alone."
Henry said to NBC at half-time that this year's UEFA Champions League "is a huge focus for us and we brought in a lot of depth to compete in both arenas."
Liverpool also parted ways with 27-year-old Uruguayan striker Luis Suarez after his infamous World Cup bite of Italy's Giorgio Chiellini, the latest in a serious of controversial moves for the Premier League Golden Boot winner.
Suarez will resume his career with Barcelona once his ban from the sport ends in October.
"It was time for Luis and time for the club to make a break," Henry said. "He brought so much to the club but we brought a lot to Luis. I think you will still see a very explosive Liverpool offense."
At Toronto, Tottenham took a 2-0 half-time edge on goals by Erik Lamela in the 16th and 40th minutes.
Andrew Wiedeman put Toronto on the board in the 65th minute and 18-year-old Jordan Hamilton netted the equalizer in the 72nd minute, only to see Andros Townsend put the winner in the upper right corner the for Spurs in the 85th minute.