Romford start the defence of their FA Vase crown with a tricky trip to Takeley on Saturday.
Boro, memorably, claimed the silverware at Wembley Stadium in May after beating Essex Senior League rivals Great Wakering Rovers.
Hassan Nalbant netted twice, either side of a Sam Deering goal, in an historic 3-0 victory at the national stadium, before captain Kris Newby lifted the trophy.
"When the third goal went in I broke down in tears, I was in bits," said Newby at the time.
"Probably the best day of my life, barring my children's birth."
But the club has seen wholesale changes since, with victorious boss Dan Spinks joining Saffron Walden Town - and seeing a string of players follow him to Catons Lane.
Newby is now the Boro manager - and enjoyed a 3-1 win over Spinks' new club less than a fortnight ago - but saw his new-look side beaten 1-0 by Rovers in a repeat of the Vase final at the Lawtech Stadium last weekend.
Harry Brown headed against the crossbar for the visitors after only two minutes, before George Martin denied Kennedy Feyi.
Praise Ogbebor was twice pulled back by Brown, who avoided a booking, but Harry Girling had to come off his line to block Callum Boylan.
Chris Millar fired over for the hosts, after combining well with Joe Paxman, while Amaree Robinson-Jones forced Martin into a good save and then grazed a post soon after.
The only goal arrived on 50 minutes when Brown stabbed home a low cross from close range.
And Boro saw Millar's shot deflected wide, Feyi head wide from Paxman's free-kick and Brendan Ocran chip over Martin and just past the post.
Robinson-Jones made way for Toheeb Elegushi - the only survivor from the squad at Wembley, where he made an appearance off the bench - with 14 minutes left, but Boro failed to hit the target at home for the first time this season.
A second defeat in 13 outings left Newby's men in fifth place, four points behind Takeley but with two games in hand.
The two sides battled to a goalless draw at Station Road at the end of August, but Takeley are unbeaten in nine matches in all competitions since - and have hit six against both Basildon Town and Halstead Town in that sequence.
"We've been dealt a really difficult tie against in-form Takeley," said Boro chairman Steve Gardener.
"There is added pressure as holders to try and get past the first hurdle. Last week saw a repeat of last year's final and Wakering came looking for revenge and edged a close game.
"It was good to see familiar faces again, but we know whether we play one game or several in the Vase, we will be the team everyone wants to beat."
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