James Thomas' brace could not save the Swans
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Southend had three players and their manager sent off but clung on to win.
Swansea's James Thomas struck first only for Leon Constantine to level.
After Dave McSweeney was sent off for kicking out at Andy Robinson, Mark Gower put Southend ahead but then Gower and Jay Smith were also ordered off.
Assistant manager Paul Brush was sent from the dug-out before Mark Warren sealed the win - even though Thomas added a late second.
Swansea: Freestone, Howard, Duffy, Iriekpen, Tate, Britton,
Johnrose, Durkan, Robinson, Thomas, Nugent. Subs: O'Leary,
Coates, Stuart Jones, Pritchard, Williams.
Southend: Flahavan, McSweeney, Cort, Hunt, Gower, Wilson,
Maher, Smith, Kightly, Bramble, Constantine. Subs: Emberson,
Broughton, Warren, Jenkins, Husbands.
Referee: G Cain (Merseyside)