From December 1959 when we won 5-4 at Preston North End with Jimmy scoring all of our goals.

From The Athletic:

THE SIX MONTHS IN ITALY

Greaves short spell in Italy poses a fantastic what-if. After all, he arrived at AC Milan at the same time as the trilby-wearing Nereo Rocco, a legend of Italian coaching, and in retrospect its hard not to wonder what might have been had the England international stuck around for longer than just four months. Come the end of the season, Milan were champions and would go on the following year to become the first Italian side ever to win the European Cup. Greaves could have been the first Englishman to get his hands on one of those medals and imagining him lifting that famous trophy aloft at Wembley of all places only adds to what is an incredible sliding doors moment. Who knows, perhaps Greaves could have won the Ballon dOr instead of Gianni Rivera.

As he packed his bags for London in late 1961, the last copy of La Gazzetta dello Sport he laid eyes on would have shown him second in the scoring charts behind the "Little Bird" Kurt Hamrin. They had gone toe-to-toe in his final game, a 5-2 win for Fiorentina, where they each bagged a brace.

In all, Greaves scored nine goals in eleven league appearances for the Rossoneri. The knock from Rocco was they tended to be scored from the penalty spot or late in the game. "This English mug," he complained. "When alls going smoothly hes brilliant. When the going gets tough, hes nowhere to be found." Fair comment, you might think, except for in the Derby della Madonnina when Greaves go-ahead goal set Milan on the way to victory against Helenio Herreras top-of-the-table Inter.

"He blew everyone away," Giovanni Trapattoni recalled in his biography Non dire Gatto. "How many goals he scored! How many defenders he sent crazy! In October (1961) he won the Milan derby for us 3-1. We were without José Altafini and Sandro Salvadore. And then no sooner did he arrive than he was gone. As a matter of fact Milan sent him back to Tottenham because he was unmanageable. He tended to drink, as the English do, and then disappear like one of those stray cats. If he could, Rocco would have throttled him. He used to yell out in his Triestino dialect and send us all over Milanello looking for him. But it was no use. You could never find him."

Not even in his room the night before a game.

"We were in a hotel on via Napo Torriani," Cesare Maldini reflected in Gigi Garanzinis biography of Rocco, El Parn. "I was in bed, Altafini was rooming with me. It was around 11 oclock at night. We were having a natter and then come midnight it was lights out. Not too long afterwards we heard a noise. From the light under the door we could see a shadow passing by.

"We got up, opened the door and there was Greaves all dressed up, ready to go out. He was carrying his shoes and tip-toeing very slowly down the corridor. He looked like the Pink Panther. They caught him in a night club in Piazza Diaz.

"The next morning Rocco sent Eugenio Conti (Milans club secretary) to wake him up and bring him to the Assassino where he was having his lunch. The whole thing was unforgettable. Greaves came in and walked over to our table. He kept his head down the whole way. He stood in front of Rocco. For 30 seconds or so no one said a word. But as soon as he opened his mouth to say sorry the storm wed all be waiting hours for finally hit. The only problem we had, I can guarantee, was keeping a straight face."

Jose Altafini, one of Greaves team-mates at AC Milan and the clubs fourth all-time top scorer. He won four league titles with Milan and Juventus as well as the 1958 World Cup with Brazil

Jimmy was a top striker. When he came to Italy he was still young but a great player. At the time he joined I thought to myself: "This guys fortissimo". But Greaves missed England. When he left in December, Dino Sani came in and took his place. Dino scored 12 goals in no time at all. He was one of the best goalscorers in the league. Sani may have arrived just as Greaves was leaving, but after seeing him in training even he said, "This guys an unbelievable player". It was true.

Greaves didnt speak Italian and because of that he was a bit aloof, which is understandable. When we went in ritiro (training camp) on a Saturday night he used to take off. Hed go to a nightclub with his wife. He thought he could do what he did in England, but not in Italy you cant. Youve got to be in ritiro until an hour before the game. Jimmy couldnt get used to that. He was a good guy, though. I liked him. It was just a shame he couldnt speak Italian. I remember a game in Venice, Milan-Venezia. We were drawing 1-1. I scored a bicycle kick and the ball looked like it might have come off him. We all ran over to Jimmy and asked him if it did or not and he said it didnt. It was a remarkable show of honesty and sportsmanship.

Rocco wasnt used to seeing someone behave like that. It was different in Italy. Players didnt go out. They couldnt go clubbing and Greaves didnt want to go in ritiro. In the end Rocco told the club it couldnt go on like that anymore. So he signed Dino Sani from Boca to replace him. Dinos debut was a game against Juve and we won 5-1. Greaves goal-to-game ratio was amazing with us. He scored nine in 11 league games. I think he got two against Inter. I was suspended but he played and scored a brace. Eleven games and nine goals isnt bad, is it? Its a bit like me in the European Cup. I scored 14 goals in nine appearances. I dont think anyones ever beaten that.
 

The other what if of course, being what if Greavsie had gone back to the Bridge…

Edited September 20, 20214 yr by Upsetter

Just watched the documentary on him on BT Sports, well recommended.

From 31 August 1958 when Jimmy donned the whites to play for Chelsea against Camberley Cricket Club, On the previous day we had beaten Wolves 6-2 with Jimmy scoring five. Not sure how many runs he scored or how many catches he took behind the stumps.