The young midfielder - on the bench at Manchester City on Sunday - has held his place in the squad for tonight's Carling Cup quarter-final against the Championship side.
Leading Southend's attack is Eastwood, the striker who grabbed all the headlines with his magnificent free-kick to knock mighty Manchester United out of the competition in the previous round.
Jamie, now 20, came across Southend and Eastwood during his loan spell at Chesterfield last season - and it's not a game he'll forget in a hurry.
Chesterfield went 1-0 up that February day, Southend came back for 2-1, Chesterfield 3-2 and finally Southend won it 4-3.
"For me personally, it was probably the best game I played in," he recalled. "My dad says to this day that it was the best I've ever played. But we had a man sent off, Freddy Eastwood scored a hat-trick and they won it 4-3.
"They were a good team but I feel we were unucky with the man sent off and that changed the game. On that day, we were by far the better team. Freddy Eastwood was the main threat, he was quiet in the first half but he then scored that hat-trick.
"We knew they wanted to get it down and play and we got into them, pressed them as much as we could and were on top. I believe if we didn't have that man sent off we would have won it.
"In the second half Eastwood came into the game and killed us, really."
So what was it about him? "He's got neat touches, he's sharp and has an eye for goal. He scored a penalty, a free-kick and one great finish, that was the second goal and it got them back into the game."
Jamie O'Hara has experienced first hand exactly what Southend striker Freddy Eastwood is capable of.