Under his guidance, the Town reached the semi-final stage in his first full campaign here, before being knocked out in the third-round last season by Peterborough United – who at the time had an attack spearheaded by former forward Jack Marriott.
The competition has seen some of the better games at Kenilworth Road during that time, and with any hope tonight's game will be no different.
Southend have got decent pedigree in the competition – although they've never lifted the trophy – finishing as runners up in 2003/04, 2004/05 and 2012/13.
The Commercial Team are pleased to advise that there is space in the Eric Morecambe Lounge for season ticket holders this evening, on a first come, first serve basis. A bar menu will be available.
Please be aware a dress code applies in the Eric Morecambe Lounge - no football shirts and no trainers.
THE GAFFER SAYS:
On progressing in the competition: "Of course [we want to make progress in the competition]. Every competition we enter we look to make progress, playing the right way, the team, everything we do. It's another good test against a Chris Powell side who are a very difficult side to play against, it'll be a real tough game.
"It was a real tough game in the league, it was a strange game actually because I felt like we could have won by more because of the chances we had on the counter, but it wouldn't have told the story of the game because it was such a tough one.
"There were probably margins in it, but we took our chances early on and then we had a lot on the counter, but they're a tough side and it'll be a tough game."
On the side he will pick tonight: "We're looking very strong squad wise, we're not that far off a full squad to pick from. Alan McCormack is the only one that is out. So we have got a good squad to choose from which is really good really, because we have got some tough games coming up, Christmas fixtures coming up.
"But after this week we have got a little bit of respite and hopefully to get a few back, so when we go into the Christmas period we will be strong numbers wise and strength wise, but we want to get through this week. We will make changes [tonight], how many will be determined on what will win us the game. there will be one or two that need the minutes, one or two that are pushing, that are so close to the first team that need their opportunity as well."
YOU CAN NOW WATCH NATHAN JONES' PRE-MATCH PRESS CONFERENCE ON IFOLLOW HATTERS FREEVIEW BY CLICKING HERE
WHO?
The Shrimpers finished second in Southern Group B, as they won two of their games, but missed out on top spot on goal difference, in a group that included Cambridge United, Colchester United and Southampton Under-21s.
WHEN AND WHERE?
Kick-off is at 7.45pm at Kenilworth Road on Wednesday 5th December.
TICKET INFORMATION
Tickets are priced at just £5 for adults and £1 for Under-16s.
For those attending tonight's game we would like to advise that unreserved seating in the Main Stand and Main Enclosure is available for home supporters.
Tickets can be purchased in advance and collected on the night. Alternatively, cash turnstiles will be in operation.
CAR PARKING
If you're driving to the game this evening, don't forget you can take advantage of the car parking now available at Power Court. Make sure you get your permit by clicking here.
FOLLOW THE ACTION
The main blow-by-blow account of the action from Kenilworth Road will be provided via the Match Centre on the club website, which you can access by clicking here. (*Please note that the club's Live Text will appear only by accessing through an internet browser, users of the Luton Town FC app will receive updates from Opta...the EFL Digital team assure us they are working on a fix to get club updates onto the app)
The main moments from the game will appear on the Hatters' social media feeds:
Twitter – @LutonTownFacebook – www.facebook.com/LutonTown/Instagram – www.instagram.com/ltfc_official/
And of course Simon Pitts will be on hand to provide commentary for iFollow Hatters which you can subscribe to by clicking here. Match passes for watching the live video stream of the match are available for £10 for domestic viewers.