The home crowd saw debutant Jack Wilshere and the fit-again Tyrone Mings complete the opening 45 minutes, before Cummings emerged from the bench for the final ten minutes to claim the MMJ Bournemouth Man of the Match award.
In what was an entertaining but competitive game throughout, three goals in five mintues ultimately decided the outcome of the game. Lys Mousett came off the bench to cancel out Suso’s opener, before Mbaye Niang’s penalty won the game for the visitors.
Prior to kick off on a mild but extremely wet afternoon, Cummings was welcomed back on to the Vitality Stadium pitch by a generous home crowd.
AFC Bournemouth’s first forray into opposition territory saw Wilshere, who three days earlier had put pen to paper on a season-long loan from Arsenal, escape in the right channel. His low cross was met by an onrushing Lewis Grabban, who directed a first-time effort narrowly wide of the post.
Up at the other end Jose Sosa arrowed a 25-yard shot comfortably over Ryan Allsop’s crossbar, in the visitors’ first effort on goal.
Wilshere’s early touches were cheered by the home support, as the on-loan Arsenal man caused problems in behind striker Benik Afobe.
On 17 minutes Wilshere combined with Junior Stanislas down the right side, before jinking beyond a marker and sending a low curling shot towards the far corner that Milan stopper Vasconcelos Gabriel did well to repel.
Stanislas went close moments later, again cutting infield from the right flank before slicing a left-foot effort wide of the far post.
Milan frontman Gianluca Lapadula cast frustrated figure up top. He chased down a long ball over the top before firing a shot wide in a rare foray forward for the Italians.
The Cherries were controlling the game. On the half hour, Grabban saw a shot cannon into a Milan defender from an acute angle.
Milan steadied the ship for the remainder of the half and arguably created the best chance of the opening period on 44 minutes. Niang latched onto Suso’s angled through ball but was denied by the sprawling figure of Allsop, as the teams headed into the interval on level terms.
With valuable match minutes under their respective belts, Mings and Wilshere were withdrawn at the break.
Bournemouth continued on the frontfoot in the early throes of the second half.
Afobe scampered down the left channel before forcing Gabriel into a smart reflex save before Stanislas, now operating on the left flank, sent a dangerous ball right across the face of the Milan six-yard box.
The Cherries upped the tempo with an opening goal seemingly imminent. Stanislas fed substitute Mousset with a clever angled ball, though the Frenchman’s shot was blocked by a last-ditch Gabriel Paletta challenge.
Mousset went closer moments later, fizzing a low drive inches wide of the far post.
But against the run of play, Milan took the lead on 64 minutes.
Suso picked the ball up in a pocket of space 25 yards out, before opening his body up and shaping a left-footed effort into the bottom corner.
But the Cherries responded immediately.
Mousset bundled his way through a couple of tame Milan challenges on the edge of the area, before unleashing a fierce drive beyond Gabriel and into the far corner.
And a frantic five-minute period culminated in the visitors regaining the lead the once again.
Niang raced onto yet another ball over the top and when attempting to round substitute goalkeeper Jordan Holmes was sent tumbling. The referee pointed to the spot, with Niang dispatching the resulting kick from 12 yards.
Much of the second half then passed without any further incident, that was until the 80-minute mark.
Cummings emerged from the bench to cheers from all inside Vitality Stadium, with his every touch from there on in lauded by the home support.
Mousset, a constant handful throughout the second period, almost equalised late on but saw his glancing header come back off the frame of the goal before rattling the post once again deep into stoppage time with a point blank effort.
AFC Bournemouth: Allsop (Holmes 46), Stanislas, Mings (Buckley 46), Jordan (McCarthy 46), Harfield (Cummings 80), Gosling, Wilshere (Mousset 46), Hyndman, Pugh, Grabban, Afobe.
Unused substitutes: Lee, Worthington, Dobre, O'Connell, Ndjoli.
AC Milan: Gabriel (Plizzari 79), Rodrigo Ely, Luiz Adriano (La Ferrara 46), Suso, Lapadula (Zanellato 61), Niang, Abate (Pogeba 90), Vangioni, Sosa, Paletta, Paselic (Curto 79).
Unused substitutes: Spinelli, Careccia, Zucchetti.
Referee: James Linington
