Tom Flanagan and Will Grigg endured Wembley heartbreak after their Sunderland side were beaten on penalties by Portsmouth in the final of the Checkatrade Trophy.
Flanagan completed the full 120 minutes at the home of English football, while Grigg lasted 77 minutes before being replaced by Max Power.
The Black Cats, who booked their place in the final with a semi-final win over Bristol Rovers, started brightly and opened the scoring after 39 minutes when Aidan McGeady curled a wonderful free-kick over the Pompey wall and into the top corner of the net.
But with eight minutes of normal time remaining, Nathan Thompson drew Pompey level with a fine header.
And after a goalless first period in extra-time, Jamal Lowe looked to have handed the South Coast club the trophy when his effort sailed over the head of Jon McLaughlin and into the net with six minutes remaining.
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But to their credit, Jack Ross' side rallied to the set-back, and with just a minute of time remaining, McGeady struck again to send the tie to penalties.
McGeady and Gareth Evans both scored their sides opening penalties, before Lee Cattermole saw his spot kick saved by Craig MacGillivray.
Brett Pitman, Lynden Gooch, Lee Brown, Max Power, Jamal Lowe and Luke O'Nien then all converted from 12-yards, before Oliver Hawkins kept his cool to score the decisive penalty and hand Kenny Jackett's side the trophy.
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