Di Canio was making his first appearance since sustaining a medial knee ligament injury in April and undergoing rehabilitation in Bologna during the summer, while Cole was back in the fray after his World Cup exploits with England, and wowed the fans at Roots Hall by sporting an eye-catching new haircut that consisted of a bright red diagonal streak across his shaven head!
Both players looked fit and sharp and lasted over an hour of this entertaining encounter. There was further good news for boss Glenn Roeder as Sebastien Schemmel also made his return from injury as a 61st minute substitute for Cole, while Di Canio trotted off to rousing applause six minutes later as Kanoute came on to partner Defoe.
The England under-21 striker had looked lively from the start, and came close to opening the scoring twice in the first 10 minutes. With just four minutes gone he latched on to Michael Carrick's sweeping pass down the left before firing in a left-foot effort that Southend keeper Darryl Flahavan did well to block.
Then five minutes later he received another pass from Carrick, before turning his marker well and getting in a low shot that Flahavan was again equal to.
Richard Garcia and Cole both had half-chances to break the deadlock early on, while the delightfully-named Barrington Belgrave should have given the hosts the lead in the 36th minute when he was put clean through but stabbed the ball wide of Raimond Van der Gouw's goal.
With just seconds of the first half remaining, though, Defoe finally got the goal his determination deserved. A loose ball in the area wasn't cleared by the Southend defence, and the 19-year-old pounced to claim his second goal in two games following Friday night's strike at Leyton Orient.
On an impressive playing surface at Roots Hall, Roeder gave the majority of his first team stars a longer run out than the 45 minutes that most had played at Brisbane Road. Defoe went close again early in the second half with a shot across the face of goal, while Di Canio forced Flahavan into a tremendous flying save with a left-foot volley that was heading for the top corner of the net.
However, against the run of play, Southend equalised with just 17 minutes left. After Repka had been harshly penalised for a foul on Belgrave, full-back Damian Searle stepped up to crash a blistering left-foot free-kick past Van der Gouw from 25 yards out.
As the Shrimpers looked content to play out the draw, though, Hammers went in search of a winner, and got their just rewards with seven minutes left when Kanoute collected a long pass in the area and crashed in a right foot shot from an acute angle.
Labant rounded things off in the final minute with a superb left-foot free-kick from 25 yards out that set the seal on an impressive performance and put Hammers back in the winning habit as the new Premiership campaign draws ever closer.
Next up in the pre-season schedule is a trip on Friday evening to Colchester United, who are managed by former Upton Park striker Steve Whitton. Kick-off is at 7.30pm.
West Ham: Raimond Van der Gouw, Tomas Repka, Vladimir Labant, Michael Carrick, Ian Pearce (Scott Minto 80), Christian Dailly, Richard Garcia, Joe Cole (Sebastien Schemmel 61), Jermain Defoe (Titi Camara 86), Paolo Di Canio (Fredi Kanoute 67), Laurent Courtois (Nigel Winterburn 45). Subs unused: David Forde, Grant McCann, Anton Ferdinand, Izzy Iriekpen, Ragnvald Soma.
Att: 8,740