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I thought Pennyfather OG was matchwinner.

Here's a bit of an article covering 1984.

Elsewhere it was generally a story of expect the expected. Third division clubs Doncaster, Wigan, and Walsall defeated fourth division Rochdale, Wrexham, and Stockport respectively. Two promoted sides - third division Hull and fourth division Darlington - beat teams from their own division in Bolton and Chester. Colchester won the Essex derby, beating Southend 3-2 after a replay, Perry Groves hitting the winner in extra-time. However, fourth division Mansfield did buck the trend, knocking out third division Rotherham 2-1.
It is interesting to note just how many column inches were given over to the FA Cup first round weekend back in 1984. Both the Daily Mirror and Express covered a lot of the games in FA Cup special sections, and these articles were not small or hidden away.
 
Answer 1. 1950

That was the first League game; we played them in the Essex Professional Cup (when it was a first team competition!) earlier than that.

Question 1 says first meeting not first League meeting as Mick quite rightly points out in which case this is the earliest I can find:

Saturday 21st December 1946
Reserve Friendly: Colchester United 2-0 Southend United.

The friendly match at Colchester was dominated by the defences, Colchester did more of the attacking and in the second half managed to overcome the defensive trio formed by Davis in goal and O’Brien and Bell at backs. The highlight for Southend was perhaps the inclusion of Trevor Bailey but he missed a “sitter”. The first goal came after 27 minutes of the second half, after a cross by Hillman the former Southend player. The Blues went within an ace of equalising when Bailey sent the ball inches wide but the result was settled shortly afterwards when the home side scored a second.
 
Question 1 says first meeting not first League meeting as Mick quite rightly points out in which case this is the earliest I can find:

Saturday 21st December 1946
Reserve Friendly: Colchester United 2-0 Southend United.

The friendly match at Colchester was dominated by the defences, Colchester did more of the attacking and in the second half managed to overcome the defensive trio formed by Davis in goal and O’Brien and Bell at backs. The highlight for Southend was perhaps the inclusion of Trevor Bailey but he missed a “sitter”. The first goal came after 27 minutes of the second half, after a cross by Hillman the former Southend player. The Blues went within an ace of equalising when Bailey sent the ball inches wide but the result was settled shortly afterwards when the home side scored a second.

Yes, but I don't think he thought reserve matches would be involved. Otherwise you would have to count hat-tricks and other stuff that happened in reserve matches. It would ruin a lot of those questions. These quizzes are always first team, unless stated otherwise.
 
Yes, but I don't think he thought reserve matches would be involved. Otherwise you would have to count hat-tricks and other stuff that happened in reserve matches. It would ruin a lot of those questions. These quizzes are always first team, unless stated otherwise.

Ok fair enough but interesting item with the Trevor Bailey connection, I think there were a couple of first team friendlies before they entered the League.
 
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