Martin Demichelis's desperate lunge on Lionel Messi at the Etihad Stadium last night resulted in a penalty being awarded and the Manchester City centre-back being handed a straight red card.

Barcelona playmaker Messi went on to score the resultant kick from 12 yards out, before Dani Alves added a second goal for the Catalans in the closing stages.

The Argentine defender is not the first Premier League player to have been red carded at a crucial stage of a Champions League tie. Here, Sports Mole has picked out five other England-based footballers that have been sent for an early bath in Europe's top club competition.

1. Jens Lehmann (Barcelona vs. Arsenal, May 2006)
The 2006 Champions League final was just 18 minutes old when the Gunners lost their German goalkeeper. He came flying off his line in an attempt to halt the onrushing Samuel Eto'o, but he only succeeded in bringing down the Barca striker just outside the penalty area. It appeared that Arsenal were going to defy the odds when Sol Campbell headed them in front just before the break, but late goals from Eto'o and full-back Juliano Belletti secured the trophy for Frank Rijkaard's men in Paris.

2. Didier Drogba (Chelsea vs. Manchester United, May 2008)
Such was the rivalry that had been assembled between between these two sides, matches would often see players from both teams square up to each other. It happened during extra time of the final in Moscow after United striker Carlos Tevez had kicked the ball out of play, rather than giving it back to Chelsea goalkeeper Petr Cech. It sparked a brawl, which resulted in Didier Drogba slapping United defender Nemanja Vidic around the face. The offence warranted a red card, meaning that Drogba was not available to take a penalty during the shootout, which Chelsea ultimately lost.

3. Rafael da Silva (Manchester United vs. Bayern Munich, April 2010)
Having been defeated 2-1 in the opening leg of the quarter-final in Germany, United responded at Old Trafford within the opening 41 minutes with a goal from Darron Gibson and a brace courtesy of Portuguese winger Nani. Ivica Olic reduced the arrears just before the break, but the hosts were still heading through on aggregate. The pendulum swung Bayern's way in the 50th minute, though, as United full-back Rafael was handed his second caution for hauling back Franck Ribery. The Bundesliga outfit made the most of the numerical advantage 16 minutes from the end as Arjen Robben fired in to send his team through on the away goals rule.

4. Robin van Persie (Barcelona vs. Arsenal, March 2011)
The Gunners took a 2-1 lead to Spain, where Messi's opener for the home team was cancelled out by a Sergio Busquets own goal. It meant that Arsenal were in the driving seat to progress through to the quarter-finals 3-2 on aggregate, only for Van Persie to see red. Having been booked earlier in the contest, the Dutch international was handed his second yellow card when attempting a shot at goal despite the fact that the whistle had been blown for offside. Van Persie pleaded his innocence by insisting that he had not heard the referee blow because of the crowd noise, but the official was having none of it. Further goals from Messi and Xavi saw Barca through against a depleted Arsenal.

5. Nani (Manchester United vs. Real Madrid, March 2013)
Sir Alex Ferguson's side collected a 1-1 draw from the first leg in the Bernabeu, so when an own goal from Sergio Ramos shortly after the restart at Old Trafford put United in front, all appeared to be going well. But, in the 56th minute, Nani, who only had eyes for the ball, caught Madrid defender Alvaro Arbeloa in the ribs with a stray boot. He was duly dismissed and United never recovered as goals from Luka Modric and their former talisman Cristiano Ronaldo squeezed Los Blancos into the last eight of the competition.