Positions with Opposite Side Castling | Chess Middlegames

Castling on opposite sides leads to very exciting attacking games. I tried to break down the common principles of playing those positions using seven game examples.

Opposite sides castling is quite different to games in which players both castle kingside. The main difference is that you don’t have to preserve your pawn structure on one side of the board. IN normal games, pushing your pawns on one side of the board would just be met by your opponent blocking you with his own pawns, which is why attempts like that are seldom made. In opposite side castling games, though, your opponent can’t do that, and your advancing pawns are going to play a role of extra attacking pieces.

That is why pawns on the side where your opponent’s king has castled are often used as battering rams, as cannon meat to open up the lines towards the king and free up space for your pieces to attack.

The second major aspect of these positions is time. Most often the games are going to be sharp, and every single tempo will count. This means that you can’t afford to waste time. Each move will have to serve a specific attacking or defensive purpose, and the side that plays slow moves without a clear goal in mind can find themselves in trouble fast. Unlike closed positions, opposite side castling positions tend to be ruthless and will seldom give you a break.

The main goal is to create an attack faster than your opponent manages to do the same to you. This will often involve removing your opponent’s defenders and getting rid of the pawns and pieces around his king, while at the same time closing the road to your own king and preventing your opponent to remove your own defenders.

I would recommend that you choose positions like these on purpose because playing them will sharpen your senses and you will be able to develop a feel for attacking play.



  1. Inspiring analysis and food for thought. My own notable lines within this theme would include the black side of the Four Knights Italian (if they don't know to retreat the bishop after the center fork trick), most lines of the Bronstein Scandinavian, the white side of the Pirc, and I'm on the black side of the Nimzo attack in the Petrov. What you said about pieces in same side attacks versus pawns on opposite side attacks resonated with me. I think I'm much better with pieces than pawn storms. Something to work on! Thank you.

  2. Thank you Stjepan. Your videos have been extremely useful for both my own improvement, as well as some of my friends’. The explanation you give of openings is already thorough, and helpful; but these middle game concept videos are uniquely beneficial. Pawn structures, opposite side castling, blundering less in general. Very helpful content.

  3. Nic (J Bruce Feynman Niccolo P. Bentulan) says:

    Consider the 90 positions in 9LX where you have to move a rook on 1 side to castle on the other side. What to do about castling then when you can't seem to keep your 'poker face' up re the video 'When to DELAY Castling in Chess!!' (5lVvs0JB5ME) ?See 'How many Chess960 positions exist in which castling on 1 side does not require moving the rook on the other side?' On Chess Stack Exchange

  4. The knowledge you share towards openings, middle games are incredible. Currently, learning the Sicilian variations from your videos. Keep up the good work!!

  5. No such thing as quoting Ben Finegold too much

  6. Thanks for this new lesson. Very useful. Regards

  7. Not only useful but also fun and interesting. Keep the good work!!

  8. Thanks for the video and your humble opinion👍

  9. Excellent explication of opposite side castling. As usual your instruction is top notch.

    I heard your interview with Ben Johnson on the Perpetual Chess Podcast. I am amazed by your personal time management abilities, and your commitment to chess improvement. I disagree with Ben. I believe you may reach your goal. Although I also feel you could become a great trainer. You make your own luck. I look forward to your analyses of your GM norms.

  10. Thank you very much for sharing your knowledge!! Your channel is so good!!

  11. I hope you become a GM and I think you should already be one!

  12. 26:30 – And here I always make a mistake and play g4… But then again, how can I attack here?

  13. Your videos are amazing thank you for putting out this material!

  14. Interesting video despite all the arguments AGAINST opposite castling .

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