Jorginho and Pierre-Emerick Aubameyang were on target as Chelsea continued their resurgence under Graham Potter with victory at San Siro.
Chelsea claimed their first UEFA Champions League win in Italy for 19 years by defeating 10-man Milan 2-0 at San Siro to move to the top of Group E.
A 4-0 win over Lazio in November 2003 represented the Blues’ last victory on Italian soil in Europe’s elite club competition, but it was similarly routine following Fikaya Tomori’s questionable red card.
Jorginho’s penalty gave the visitors the lead in the 21st minute after former Chelsea defender Tomori was sent off for a foul on Mason Mount in the box.
Pierre-Emerick Aubameyang then doubled the lead before half-time, enough to send Graham Potter’s side top of the pool after Salzburg’s 1-1 draw with Dinamo Zagreb.
Milan were reduced to 10 men in the 18th minute when Tomori was controversially shown a red after tangling with Mount in the box as the Chelsea player shot through. Jorginho then calmly sent Cipriano Tatarusana the wrong way from the penalty spot.
Olivier Giroud, another ex-Chelsea player, wasted a golden opportunity to equalize for Milan in the 27th minute when he headed home Brahim Diaz’s tantalizing cross from eight yards.
And the Rossoneri were to rue their waste as Chelsea doubled their lead seven minutes later. As in the 3-0 win at Stamford Bridge six days earlier, Aubameyang netted the second with a clinical finish from Mount’s neat clearance.
Substitute Conor Gallagher came close to adding a third within four minutes of the restart but could only find the side netting, while Aubameyang drew smart reflexes from Tatarusanu.
While Sergino Dest fired at the other end and the Rossoneri fell to their fifth home defeat in six Champions League games against English opposition, the only dampener for Chelsea was an injury to England right-back Reece James.