Crouch scored with 10 minutes remaining after Aaron Lennon had broken clear from his own half.
Zlatan Ibrahimovic thought he scored an injury time equalizer, but his overhead kick was ruled out for a push on Spurs captain Michael Dawson.
Milan captain Gattuso, who had earlier shoved Jordan during the match, was also booked in the 75th minute and will miss the return leg at White Hart Lane.
It was an unseemly end to a match in which Tottenham again impressed at the San Siro, having recovered from 4-0 down to 4-3 against Inter Milan in the group stage earlier in the season.
Crouch was picked up front, with Jermain Defoe on the bench, and Harry Redknapp had clearly set up his side to target Crouch's height as a way to trouble the Milan defense.
The England international came close to scoring in the fifth. Vedran Corluka crossed from the right, Crouch won the ball in the air, but his shot lacked power and was easily held by Milan goalkeeper Christian Abbiati.
The pair nearly combined again four minutes later when Alessandro Nesta failed to head clear, but Abbiati reached Corluka's cross as Crouch was poised to head on goal.
Abbiati stopped Tottenham again in the 11th. Corluka released Lennon on the right and the goalkeeper pushed away his cross, with Luca Antonini clearing the danger.
Corluka and Crouch then combined to set up Rafael van der Vaart for a shot, which Abbiati held. It was Abbiati's last major contribution though. Shortly afterward he was stretchered off after colliding with Crouch while challenging for a ball in mid-air and replaced by Marco Amelia.
Finally Milan created a chance, but Spurs goalkeeper Heurelho Gomes blocked Ibrahimovic's powerful effort from the left.
The Swede then felt he should have had a penalty after he went down under a clumsy challenge by Sandro, but referee Stephane Lannoy waved away Milan's appeals.
Tottenham continued to keep the host pinned back and Van Der Vaart had a shot tipped over the bar for a corner by Amelia.
Alexandre Pato replaced Clarence Seedorf at the break, but Tottenham had the first chance of the second half as Van Der Vaart chipped narrowly wide.
Milan hit back immediately. Gattuso crossed from a poorly cleared corner and Gomes scooped Mario Yepes' powerful header out from under the bar.
The match began to increase in tempo and Mathieu Flamini was booked for a foul on Corluka that led to the Croat being carried off on a stretcher. He returned to the bench on crutches with his right foot bandaged.
The Brazilian again denied Yepes in the 60th diving to his right to block the Colombian's header after Thiago Silva had whipped in a corner.
Spurs scored when Lennon led a counterattack from his own half. After rounding Yepes and drawing Nesta, he squared across goal for Crouch to have the simple task of slotting the ball low past Amelia into the corner of the goal.
In injury time Dawson came to his side's rescue when he flung himself at Robinho's shot before Ibrahimovic's acrobatic effort was ruled out.
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