There's surprisingly little head-to-head history between either Antonio Conte and Jose Mourinho, and Chelsea Football Club and Jose Mourinho. Okay, maybe it's not so surprising, given Conte's managerial beginnings in the lower divisions of Italian football, and the a long shared history between the latter pairing that reduced opportunities for clashes outside of those friendly confines.
Incidentally, all three total meetings between the three parties in question, in various combinations, occurred back in the 2009-10 season.
2009.XII.14: ATALANTA 1-1 INTERNAZIONALE
Jose Mourinho's Inter Milan side traveled the short distance east to Bergamo to take on Atalanta, managed by Antonio Conte in his first stint in top flight management. The previous season the current Chelsea head coach had guided Bari to promotion from Serie B, but left the club in the offseason by mutual consent after it looked like Juventus might offer him the job. As it turned out, Juve went with another former player, Ciro Ferrara instead, and Conte was left holding his bags, homeless. A month into the season he took over struggling Atalanta, but failed to improve their fortunes. Things got so bad that at one point he even required police protection from the club's Ultras; Conte resigned in early January.
He's experienced nothing but success since, and the 1-1 draw he eked out against Inter just before his resignation was a sign of things to come. There should've only ever been one possible outcome between Inter, future champions already top of the table, and Atalanta, on their way to relegation already bottom of the table, but while Inter dominated for large swathes and hit the post twice, they also got lucky multiple times to keep the ball out of their own net. Mourinho's men were reduced to 10 in the second half when Sneijder was dismissed and Conte's men grabbed the equalizer through substitute Simone Tiribocchi.
Atalanta's lineup consisted basically of complete unknowns (other than CM 01/02 all-star Giampaolo Bellini and once highly promising Robert Acquafresca) but their effort was praised for tenacity, grit, and tactical intelligence against Inter's collection of Mourinho zealots (including future Chelsea striker Samuel Eto'o).
Incidentally, both Mourinho and Conte were banned from the touchline in this game. I'm not sure why that was for Conte, but Mourinho was serving the ban due to being sent off the in previous match against Juventus for sarcastically applauding the referee. Mourinho would get into even more hot water afterwards — this was a daily feature of his time in Italy — when he was accused of physically assaulting a reporter. While Jose admitted verbal abuse, he denied the physical altercation. Later that season he would be banned for three more games for a handcuffs gesture. It would be his final season in the Serie A, though he ended it on historic note by winning the Treble.
2010.III.16: INTERNAZIONALE 2-1 CHELSEA
Mourinho's path to the Champions League crown went through Chelsea, who at the time were managed by fellow Italian Carlo Ancelotti, a rival from his days in Serie A with Inter's arch-rivals AC Milan. Ancelotti claimed "the whole of Italy" were rooting for him and Chelsea over the increasingly controversial Mourinho. Alas, Mourinho out-tacticed and out-lucked Ancelotti.
Recently retired Diego "The Prince" Milito staked the host to an early lead and while Salomon Kalou equalized for Chelsea (good work, Branislav), and Walter Samuel got away with a clear penalty, it wasn't to be Chelsea's day. Still, the 2-1 first leg away result in the Champions League knockout round wasn't the worst and there was everything to play for in the second leg.
2010.III.24: CHELSEA 0-1 INTERNAZIONALE
Alas, as is his wont, when the chips are down and a result must be achieved, more of then than not, Mourinho emerges triumphant. And so it was for these 90 minutes, with the visitors putting in a classic spoiling, counter-attacking performance against Carlo's would-be Premier League champions. Toothless Chelsea, with Samuel getting away with another clear penalty offense (where were you at, UEFAlona?) eventually gave up a winner to Eto'o (oopsies, Branislav) and the ignominy of the night was complete when Drogba was sent off for a stamp on Motta in the dying minutes.
That night started with a warm welcome for Mourinho and ended in disappointment and harsh feelings. What fun does Sunday have in store fore us?