The 2013-14 Academy season began with a trip to Northern Ireland as Liverpool competed in the prestigious Milk Cup. An U17 side coached by Mike Garrity took part in the competition, however this was mostly composed of U18 squad players. Initially, the Milk Cup sees all 20 club sides compete together in one group, however each team only has to face a random selection of three opponents. Liverpool finished fifth, narrowly missing out on a place in the Milk Cup proper, however they qualified for the secondary tournament- the Milk Cup Globe- which they went on to win. Garrity led the U18s as their league campaign kicked off, replacing the recently-departed Steve Cooper, until the Reds recruited a new full-time U18s coach in the shape of Crewe Alexandra's Neil Critchley.
Critchley oversaw the Reds compete in the top tier of the U18 Premier League. In this season, the Reds played home and away matches against other top tier Northern U18 Premier League sides, and one match against each of the Southern U18 Premier League sides. A leaky defence proved costly in the season as Liverpool finished third in the division, missing out on a place in the season-ending knockout stages. The Reds also toiled in the Youth Cup- crashing out at the quarter final stage after falling to Reading on penalties. In attack, Harry Wilson- who early in the season had become the youngest ever player to feature for the senior Welsh national side- and Jerome Sinclair led the goalscoring charts with 14 goals each in all competitions. Sinclair's goalscoring was particularly impressive, with him clocking up his 14 goals in just 18 appearances.