The Three Lions face Italy in their final Group B game on Wednesday evening, knowing that a win will take them into the semi-final.
England v Italy
UEFA European U21 Championship
Group B
7.45pm (BST), Wednesday 24 June 2015
Ander Stadium, Olomouc, Czech Republic
Live on BT Sport
Even a draw could be enough to progress, depending on the outcome of the other fixture between Portugal and Sweden, but a second defeat would see England heading home early.
And that’s something which Chalobah wants to avoid, having been part of the U21 squad that exited the Euros in 2013 at the first stage after three defeats in Israel, along with current squad-mates Jack Butland and Nathan Redmond.
"After being in the last tournament and the pain we experienced after not winning a game, me, Jack Butland and Nathan [Redmond] try to pass on as much as we can to the lads," said Chalobah.
"It wasn’t very nice, so we try and let the lads know how much it hurt us and we don’t want to feel that way again.
"It was my first time in the U21s squad and it was our first game in the tournament against Italy.
"It was disappointing that we lost that game, it always hurts losing, but we’re just focusing on ourselves for the next game.
"It was good to get the result the other day and now we can hopefully kick-on tomorrow and get another one."
The importance of this game isn’t lost on the 20-year-old, who is still eligible to play for the U21s again in the next Euro campaign, though.
With three points in the bag, if England can repeat their victory against Sweden from Sunday, then they will be through to Saturday’s semi-final.
But after picking up a draw in their game with Portugal on Sunday, following their opening day reverse against Sweden, the Italians also know that a win could still see them qualify for the next stage.
"It’s a very big game because we know we could potentially be two games away from being European champions if we win tomorrow," added Chalobah.
"But it is the final stage of the competition and every team that got here deserves to be here, so I don’t think any team is going to be a pushover and you can see that in both groups.
"There was a lot of pressure going into the [Sweden] game, but we’ve got to go out there and keep mentally focused on our performance.
"We can only go into the game and take as much confidence as we can from the last game to get the result.
"We stick together as a group and we’ve been together for two years now, we get on really well on and off the pitch and that plays a massive role in the sense that when we go on the pitch, we give it everything that we’ve got.
"It’s so important that we stick together again, focus on the next game and go again."