Maidenhead United v Portsmouth
Saturday November 10, 12:30
Live on BT Sport
Out of form Maidenhead struggling
This will be the first ever meeting between Maidenhead and Portsmouth in the FA Cup, and it could well be the biggest game in the Magpies' history. The hosts are managed by Alan Devonshire, and if you are not old enough to remember "Dev", he played for my team West Ham in the golden period of the 1980s and was truly one of the most wonderfully gifted midfielders who, like many creative players of that era, was largely ignored by the national team.
Devonshire returned to Maidenhead for a second spell in 2015 and led the team to a highly creditable top-half finish last term. A fine achievement considering Maidenhead are one of the only sides at National League level that are made-up of part-timers.
It looks as though this term will be a season of struggle. They head into this game following six league defeats on the spin.
Will a Cup run be required by Jackett?
This is a big campaign for Kenny Jackett and Portsmouth regarding automatic promotion. In their quest for that, they are in pole position at the moment as the League One leaders with 38 points. You can back Pompey in the Winner market with odds of 4.30100/30, although Sunderland are still the favourites.
The Fratton Park club have been eliminated in the FA Cup first round in five of their last six campaigns, and it most certainly is the poser regarding the visitors as to what sort of team Jackett will field considering promotion is the main aim. He led Millwall to a semi-final in 2013, and Pompey won the trophy in 2008.
Devonshire has recently signed Bristol Rovers' defender Alfie Kilgour on loan and is eligible to play. Portsmouth could unleash on-loan Aston Villa winger Andre Green - who has recovered from an operation from earlier in the season. Fellow loanee Ben Thompson (Millwall) has also been granted permission to play.
Massive price on hosts is not tempting
These games are never easy as they are so lop-sided. Portsmouth trade at 1.282/7 and you certainly don't need me to tip them up at such a low price. Likewise, Maidenhead are chalked up at 13.50 but could be even bigger on their recent league form. That includes a couple of heavy defeats at 0-6 and 0-7. In truth, they could be 20.019/1 and no one would bat an eyelid.
There isn't really a trading angle with the hosts either. If they score early, Portsmouth will still be expected to win the game, so there won't be much of a shift from the 13.50 price. This will be the York Road club's 10th appearance in the first round - a stage they have never progressed from.
Maidenhead will be up against a mean defence too; Pompey have never conceded two in a game on the road this term and have three clean sheets away. Only Sunderland have conceded fewer in the division.
It's a market for the money-buyers. Maybe the odds-on backers can spend their winnings in the world-famous Fat Duck restaurant nearby?
Leaky home defence a guide to Overs
Playing the Over 2.5 market at around 1.654/6 might pull a few in considering Maidenhead's leaky defence. The hosts have already shipped in a total of 41 goals so far this season in 19 games. It's an even split in terms of home (20) and away (21). Devonshire will set them up to be hard to beat and stay in the tie for as long as possible - which will not be easy for a team that recently conceded six against AFC Fylde.
One of their big defeats at 7-0 might be a touch misleading as United had their goalkeeper sent off on 36 minutes. However, their defence is in stark contrast to Pompey's - who are very miserly. Typical of a Jackett team, he's a manager who spends hours on the training ground on shape and tactics as he likes to control games. Like Rafa Benitez.
Pompey have some tremendous attacking talent if you are looking at this market. Jamal Lowe and Ronan Curtis are the south coast's club leading scorers with six apiece. You would be pretty disappointed if they couldn't score against an opponent who ship goals for fun.
Pompey good enough to cover the handicap
There are various ways of trying to boost the ultra-short 1.282/7 for an away win. The 2.5 angle is a possibility, but a bit more bang for your buck is the Portsmouth -1 market at around 1.774/5.
I prefer this to the Win Both Halves market. Portsmouth do have a tendency to struggle with killing teams off. They beat hopeless Bradford last weekend 1-0 and couldn't get the second. It was the same against Gillingham and Accrington previously, and it has been mentioned they can improve in the final third. But with the realistic hat on, Maidenhead are considerably weaker than their recent opponents.
I flagged up Burton's Liam Boyce in a recent EFL Cup preview, and backed him to score at anytime. To see him miss a penalty was a real kick in the teeth, but it's a market I am keen to have a look at once again.
I've mentioned Pompey's Jamal Lowe. He's an excellent player who can cut in from the right, whilst Ronan Curtis has been earning rave reviews since his switch from Derry City. The 22-year-old has been linked with Leeds, Sheffield United and Leicester recently - although I liked his response to the transfer speculation by saying: "I've only just got here!"
Curtis and Lowe are both 10/3 for First Goalscorer.
Whether Jackett starts Oli Hawkins is a poser. The giant centre-forward has three in three but he does miss a few chances. I wonder if Jackett will give the wily old forward Brett Pitman a run-out.
The 30-year-old was on the bench last week but has scored four in 14 this term. He's a subtle finisher and lethal in front of goal. Hawkins fits a system that Jackett gets the best out of, but the 10/11 Anytime Scorer on the Sportsbook is worth a look.