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Basically what I am trying to ask is, can I use expression an expression like

... in the same season when she won the title.

instead of

... in the same season she won the title in.

I can extend these examples for same day, same year

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My impression is that lots of native speakers do this (see Ngram), but that lots of other native speakers consider it wrong and may correct you. You should use "same season as", "same season that", or just "same season". – Peter Shor Dec 23 '12 at 13:57
To add to what Peter Shor has said in his comment, I think the same as is a common pattern and most people would accept it. So I would consider the following sentence to be correct (unless I am corrected by someone): He won the Grand Slam in the same season as she won her maiden title. – user32480 Dec 23 '12 at 14:15
Ignore my above comment; I haven't found any websites saying these constructions are ungrammatical (even though it seems to me that this is just the kind of thing the grammar police would like to criticize). – Peter Shor Dec 23 '12 at 16:07
up vote 2 down vote accepted

... in the same season she won the title in.

makes a redundant use of the preposition in. You used it twice when you only needed it once.

... in the same season when she won the title.

is fine, but most people would elide the when and just use the second form without the redundancy:

... in the same season she won the title.

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The second "in" is not redundant. In the sentence "He quit playing in the same season she won the title in", the first "in" applies to the his quitting playing, and the second to her winning the title. This sentence is confusing you because you don't need either "in" here, and can drop both of them. But consider the sentence "He jumped out of the same birthday cake she jumped out of". If you try to drop the second "out of", you get "He jumped out of the same birthday cake she jumped", which is ungrammatical. – Peter Shor Dec 23 '12 at 14:05
@PeterShor: It is possible to postulate a sentence in which the second preposition is not redundant. But since we don't have the antecedent to deal with in the OP's example, I went with the simpler and more obvious; in your example, most people would phrase that sentence as "He jumped out of the same birthday cake she did," simply to avoid what is at least repetition if not actual redundancy (though I still feel it is). – Robusto Dec 23 '12 at 14:11
I'd say you want to drop the second in not because of redundancy, but repetition. So I would say it's not ungrammatical with the second in, but it is bad style. Giving the wrong reason for the right answer can confuse people learning of English. – Peter Shor Dec 23 '12 at 14:22
@PeterShor: With all due respect, we are arguing about semantics. Redundancy is always repetition, and repetition is redundancy when it is unnecessary, superfluous, verbose, or tautological. In the cases I mentioned, it is unnecessary and verbose. I still maintain that mine is the right answer for the right reason. You're a well known math genius — doesn't the simpler explanation seem preferable to you? – Robusto Dec 23 '12 at 14:30
You didn't actually need the in at all; they're both unnecessary and verbose: “He won the Grand Slam the same season she won her maiden title.” – Peter Shor Dec 23 '12 at 15:21

In the same season when she won the title is at best informal. It may even be ungrammatical, and, if so, others may be able to say why.

In the example in the same season she won the title in, you certainly can’t repeat in, but you can say

in the same season in which she won the title,

in the same season that she won the title or

in the same season she won the title.

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Or just "the same season she won the title". All the in's are unnecessary here, which is the only reason why you can drop the second one. "She arrived in the same limo that he arrived" doesn't work. – Peter Shor Dec 23 '12 at 14:10

I would generally say

the season when ...
the place where ...

but one of

the same season that ...
the same season as ...
the same place that ...
the same place as ...

From some experiments with Google Ngrams, it appears there are lots of other people who do the same thing I do, but there are also lots of who have no problem with "the same place where" or "the same time when". I have not been able to find any websites calling "the same place where" or "the same time when" ungrammatical, so I would say that they are undisputedly grammatical.

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Can you explicate that “I would say X but one of Y” structure? Presumably you intend for some elided something to be understood in second clause, but what? – jwpat7 Dec 24 '12 at 0:03
I meant that without the adjective "same" I would use "when" or "where", but with "same", I change the conjunction to either "as" or "that". – Peter Shor Dec 24 '12 at 0:11

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