The Imps secured their passage to the next round thanks to a 5-0 mauling of Bradford City, ensuring Jurgen Klopp’s men face League One opposition in the third round for the second successive season.
It is an occasion which is set to see the Reds field a much-changed, albeit still senior, side, with the fixture sandwiched between Premier League meetings.
The matchup presents another tantalising challenge in what has been a memorable three years for Lincoln, who in 2016/17 were members of the National League.
Two promotions in four seasons now has them settled in League One for the second year running and their confidence is high after starting the new campaign with five victories across three competitions.
After Appleton retired from professional football in 2003 following spells with Preston North End and West Brom primarily at Championship level, he immediately turned his attention to coaching.
The former midfielder, who was once on Man United‘s books, started at youth level with the Baggies before moving up the ranks and was sensationally named caretaker manager for the first team in 2011 after Roberto Di Matteo was sacked.
Since then, the 44-year-old has taken charge of Portsmouth, Blackpool, Blackburn and Oxford, and spent time with Leicester as Craig Shakespeare’s assistant which led to another brief stint as caretaker manager, with the Foxes winning both matches.
Throughout his managerial career, he has been relegated and had two spells which lasted no longer than 67 days (Blackpool and Blackburn), but it was with Oxford where his greatest success arrived as his side achieved automatic promotion to League One and reached the final of the EFL Trophy.
And now he is in his second season as Lincoln manager, with his first campaign, which he started in mid-September, ending with a 16th-placed finish in the third tier after the premature end of the campaign.
A host of summer signings have now been made as Appleton looks to continue Lincoln’s upward trajectory.
LNER Stadium, commonly referred to as Sincil Bank, will, of course, play host without fans due to the government’s guidelines for the pandemic.
The stadium has been home to the Imps since 1895, with Lincoln previously having played nearby at John O’Gaunts from their inception date in 1884.
The ground can currently hold 10,120 fans, but the club remains “optimistic” over plans to increase capacity by at least 1,500 despite the financial implications of COVID-19.
While the majority of Lincoln’s team will be unrecognisable for Liverpool supporters, there are a number of faces the Reds have come across in recent years.
Liam Bridcutt is one such player, with the defensive midfielder having faced off against the Reds on five separate occasions – with Sunderland in the Premier League in 2013/14 and 2014/15 and with Brighton in domestic cup action in 2011/12.
The 31-year-old never tasted victory in any of those meetings (D1, L4), but will now look to plot Liverpool‘s downfall as captain of the side, having recovered from a hamstring injury to feature against Bradford in his first game since sealing a permanent switch to the club.
Likewise, former MK Dons midfielder Conor McGrandles and defender Joe Walsh have recent history with Klopp’s men having played the full 90 minutes against the Reds in last season’s third-round tie at Stadium MK.
Walsh and McGrandles joined fellow League One side Lincoln permanently over the summer, with the latter set to become a key player in an attacking midfield role for Appleton.
The summer window has seen Appleton required to search for new attacking impetus, with last season’s leading goalscorers Tyler Waler and John Akinde having both moved on.
Striker Callum Morton, who scored the final goal in the 5-0 win over Bradford, was acquired on loan from West Brom.
But the manager has since identified the need for another versatile forward this summer with the aforementioned departees taking 24 total goals from a side who scored 52 across all competitions in 2019/20.
The League Cup meeting between the two clubs will be the first in an official capacity since February 1961.
The pair have battled it out a total of 23 times in their history between 1893 and 1961, primarily in the Second Division with only three meetings coming in the FA Cup.
Liverpool have the bragging rights with 13 victories while another five ended in a draw, with the last meeting in the Second Division in 1961 seeing Bill Shankly’s side emerge as 2-0 victors.
Lincoln would be relegated to the Third Division come the end of that 1960/61 season before subsequently dropping to the Fourth Division, while the Reds would rise under their legendary leader to clinch their sixth First Division title in 1964.
This will, therefore, be the first meeting between the two clubs in the League Cup – a competition Liverpool have won on eight occasions and one Lincoln have never progressed beyond the fourth round, which they achieved once in the 1967/68 season.