The Reds finished eighth in the Premier League last season with a 14-14-10 record. Perhaps more worrying, Liverpool finished four points behind seventh-place city rival Everton.
On the positive front, the Reds won the League Cup to secure a berth in the Europa League.
New manager Brendan Rodgers and his 30-plus squad were slated to leave Liverpool's John Lennon Airport on Monday for a North American tour that features games against Toronto FC on Saturday at the Rogers Centre, AS Roma at Boston's Fenway Park on July 25 and Tottenham at Baltimore's M&T Bank Stadium on July 28.
Liverpool will be based at Harvard in Cambridge, Mass. Boston is home to the club's owners, the Fenway Sports Group.
The Liverpool tour squad includes new signing Fabio Borini, an Italian international forward.
Striker Andy Carroll, whose 35-million-pound (C$55.5 million) price-tag has produced 11 goals in 56 games, is reportedly set to join the team on July 23 — assuming he is still in the picture.
Carroll has been linked to a variety of clubs in recent days.
The tall England international with the ponytail reportedly earns 80,000 pounds (C$126,950) a week. In contrast, Toronto's highest-paid player — captain Torsten Frings — makes about C$47,000 a week according to the MLS Players Union website.
Frings is the exception rather than the MLS rule, however.
Sixteen TFC players make less in a year than Carroll does in a week. Toronto goalie Milos Kocic, for example, has an annual salary listed at US$44,100.
British reports say Rogers was given 30 million pounds (C$47.6 million) plus whatever he makes from players sales to bring in new talent.
The 39-year-old manager, who won kudos for his work with Swansea City, succeeds Kenny Dalglish, who was fired in May.
Those on the plane have plenty of incentive, according to Liverpool legend Ian Rush.
"Everyone will be fighting for a place under the new manager," the former star striker and current Liverpool ambassador told The Canadian Press in a recent interview.
Liverpool's first trip to North America since 2004 is more than just a training camp. It's a chance to further promote the worldwide brand of a storied franchise whose trophy case includes 18 league championships, five European Cups, three UEFA Cups, seven FA Cups and eight League Cups.
While the last European Cup came in 2004-05, Liverpool has not won the league since 1989-90.
Still, the team remains a favourite around the globe.
"For me, the world is not a big place anymore — it's a small place," Rush said. "When you realize the history of Liverpool football club, that is something you cannot buy. You've got the famous Kop (stand at Anfield) and the famous song 'You'll Never Walk Alone. This is the history of Liverpool football club."
Rush believes it is even more important these days for Liverpool to travel the world and go to its fans.
"They've stuck with the club when times have not been as good as they would have liked them to have been. And for me that makes it even more successful, because when you're winning it's very easy. It's when you're not winning, that for me is when you stick together even tighter and you work harder. I think that's what the supporters have been worldwide."
Now it's up to the players to entertain the fans, says Rush who has seen Liverpool shirts from Africa to India.
Rush believes the Reds are the best supported club in the world. But he realizes that trophies are needed to keep the fan base growing.
"We need to get a different generation, a younger generation (of fans)."
A younger generation of player, meanwhile, is learning the responsibility of pulling on a Liverpool sweater, said Rush.
"You've got to play well ever game for Liverpool. You can't play three out of six games well because then you become a normal club."
People demand instant success these days whether they are fans or owners, said Rush.
"Look at (Manchester United's) Alex Ferguson, probably the most successful manager," Rush said. "It was five years before he won anything. Today's world, that will never ever happen. They want instant success and that's what it's all about now ... Sometimes you have to be patient. And if you see things going the right way, then you have to be patient with them.
"It's no good chopping and changing all the time."
It's advice that Toronto FC has perhaps learned the hard way, with seven managers in six MLS seasons and no playoff berth to show for it.
Rush, 50, never visited North America during his playing days, missing a Wales tour of the Canada in the early '80s due to injury.
Signed from Chester in 1980 for 300,000 pounds (C$476,100) — then a British record for a teenager — Rush went on to score a club-record 346 goals in 660 appearances for Liverpool.
The Welsh star had two stints at Anfield, from 1980 to 1987 and 1988 to 1996, sandwiched around a brief time at Italy's Juventus.
He also played for Leeds, Newcastle, Sheffield United, Wrexham and Australia's Sydney Olympic before retiring in 2000.
Rush scored 28 goals in 73 appearances for Wales.